Farm visit prep · Waterloo · August 2026
The briefing panel
Hosts, network, product facts, and the game plan for the overnight at The Battle Field Farm House. People and repo facts verified 23–24 Aug 2026.
The one thing to internalize: you are not visiting a retired founder. Chris is 6 months into being a full-time startup CEO again (twelvesenses), Diana runs a consultancy and is his CPO, and the whole ex-Waeg crew operates as one connected unit: consultancy funds and staffs the studio, the studio funds the startups, the farm is their shared stage. Mentoring founders is literally one of Chris's stated occupations. Your ask fits what he already does on purpose.
Your common ground is real but thin: 3 years as a Salesforce Architect at Waeg, 5 years total on one ex-Waeg client Chris knows well. You barely spoke personally back then, so treat this as building a relationship, not resuming one.
New since the first brief: Ivo Costa reached out on WhatsApp, hopes "we are going to work together," and hinted you could "be part of something exciting." He will not be at the farm, but Chris and Diana almost certainly know what he means. Expect the topic to surface; your holding response is in the Game plan tab.
Timeline: Waeg to now
- Chris founds Waeg while still doing hands-on Salesforce delivery at Electrabel. Grows it to ~200 people, 7 countries, Platinum partner.
- Diana joins Waeg as a CX design / change management consultant (she was a graphic designer in Bucharest before that).
- IBM announces the Waeg acquisition, its second Salesforce partner buy that year. Price never disclosed. Brand survives as "Waeg, an IBM Company."
- Earnout years. Diana rises to Head of Consulting, then COO (Feb 2023).
- Diana leaves and co-founds MavenHive with Jens Vanden Meersschaut.
- Chris exits IBM. Weeks later co-founds FoundersOhana, a community for founders who sold their companies.
- Chris invests in Learnr.be, then joins Diana's company as director. MavenHive rebrands to The Octopus Consulting.
- Chris and Ivo Costa start Octopus Venture Studio in Waterloo.
- "The Battle Field Farm House by Octopus" opens as their customer and partner venue.
- CES: twelvesenses go-to-market launch, "in partnership with Octopus Consulting, funded by Octopus Venture Studio."
- Chris goes full-time founder/CEO at twelvesenses; Diana adds the CPO hat.
- You visit. Octopus Consulting is meanwhile hiring a Business Development Director.
Chris Timmerman
| Now | Founder/CEO twelvesenses.ai · co-founder Octopus Venture Studio · director at Octopus Consulting · co-founder FoundersOhana · investor/advisor Learnr.be |
| Base | Brussels / Waterloo |
| Education | MBA, Cass Business School London (entrepreneurship + international business) |
| Communities | Entrepreneurs' Organization Belgium (loves the retreats: sailing in Knokke), PEF Community |
| Self-description | "Strategic risk taker, optimistic contrarian, and hyperactive doer!" |
Two things about his past matter for how you talk to him. First, he was a delivery person before he was a CEO: six years as a business analyst and program manager at Electrabel, shipping 20+ force.com apps with SAP integrations. He will actually understand SalesPros at the feature level. Second, his own explanation of Waeg's success is people-first culture, not sales genius, and he repeats it consistently:
"Putting people first, whether team members or clients, creates the foundation for a truly successful and profitable business."— his LinkedIn Waeg retrospective
What he posts about lately
- Deskless workers as the frontier: "Over 70% of work is done deskless." Wearables, voice, agentic support in the moment of work.
- The "Donna" demo: a voice agent for Salesforce field service, run live over dinner at the farm. Engineer prepares for a visit, closes the case, and triggers invoicing entirely by voice.
- CES takeaways: Europe at the AI forefront, AI-led factories with digital twins, industrial smart glasses going pervasive.
- Venture-studio wins (Learnr's third customer) and EO Belgium community life.
Diana Graur
| Now | CEO & co-founder, The Octopus Consulting · CPO, twelvesenses (since Apr 2026) |
| Base | Brussels; originally from Romania (Bucharest Academy of Economic Studies) |
| Waeg years | 2016–2024: CX consultant → practice lead in Waeg Envision (strategy division) → Head of Consulting → COO |
| Before Waeg | Graphic/brand designer: ad agency account work, freelancing, lead designer for IMWorld (Romania's biggest tech expo) |
Her arc is the unusual one: designer → CX consultant → COO → CEO, no technical background, which makes her the strongest person in the room on positioning, customer experience, adoption, and brand. She rebranded her own company once already (MavenHive → Octopus) and clearly enjoys marketing stunts (the "Octotruck," a free-first-Agentforce-use-case Black Friday deal, DJing at Salesforce community parties).
"If you never get booed, you're not really taking any risks over there, are you? Get booed. Bonus points if they throw vegetables."— her LinkedIn post on becoming an entrepreneur
Same post, the serious part: she once thought she lacked the charisma and risk appetite to be a founder, and the unlock was surrounding herself with complementary people instead of doing everything alone. That is almost exactly your situation in mirror image (you have the product depth, not the GTM), and she is likely to recognize it.
The Octopus Consulting Salesforce Summit Partner
| What | Senior-only Salesforce boutique, "Building what's next with Salesforce" |
| Size | ~20–30 people; hiring bar is 5+ years of Salesforce, team averages 12 years, 150+ certs |
| Offices | Gent (BE) and Lisbon (PT) |
| Clients shown | IMCD, SD Worx, EQUANS, Statamat, B&C |
| Founded | May 2024 as MavenHive (Diana + Jens); rebranded Nov 2024 when Chris joined |
Four offerings: end-to-end implementation; org audit and technical-debt cleanup (positioned against sloppy prior partners); AI governance ("Agentforce with EU AI Act included"); and the differentiator, wearables + voice AI for deskless workers. Their demo wardrobe includes Vuzix and INMO smart glasses, watches, and smart rings. Notably, the smart-glasses demo runs Claude-powered on-lens diagnostics against live Agentforce/Salesforce data, "cited down to the page."
Recent activity: sponsored Salesforce Summit Netherlands (Hilversum, May 2026), presented at the Agentforce Service Demo Jam (Mar 2026), joined a Portugal–Sweden trade mission (they seem to be probing the Nordics from the Lisbon office), and are currently hiring a Business Development Director in Brussels. Growth mode, sales-capacity constrained.
Octopus Venture Studio
| What | Purpose-driven venture studio: "every venture has a positive impact on people, society or our environment" |
| Who | Chris + Ivo Costa; 2–10 people; HQ Waterloo, founded Jan 2025 |
| Model | Studio-led (in-house ideas) and founder-led (founders join at concept-validation stage; studio helps prove product, demand, pricing, business model) |
| Known bets | Learnr.be (e-learning for police/fire/emergency), twelvesenses, STRAELA (site testimonial) |
No published check sizes, no application process, zero deals recorded on PitchBook. Read it as a personal vehicle for backing people they know, "financially, strategically and operationally" (their words about Learnr). This confirms your instinct: funding here would follow a relationship, never a pitch deck. Don't treat it as a fund; treat it as what mentorship looks like when Chris commits.
twelvesenses.ai stealth-ish
| What | "AI-Powered Risk Intelligence for Deskless Workers. Predicting human operational risk before it becomes an incident." |
| Product | The "Artificial Thalamus": a layer between people, equipment, and enterprise systems; fuses wearables, cameras, sensors, and business platforms to predict fatigue, distraction, unsafe adaptation. Names Salesforce, ServiceNow, and SAP as systems that can receive events. |
| Team | Chris (founder/CEO, full-time since Mar 2026), Ivo Costa (co-founder/COO), Diana (CPO). "A founder-led team building the leadership that will take this to market" |
| Stage | Very early: Delaware C-corp, offices "to be disclosed" (SF, Lisbon, Dublin), demo-driven sales, NVIDIA Inception member, LinkedIn page has 18 followers and zero posts, no press found |
| Framing | 80–90% of workplace accidents are human error; 5,070 US occupational deaths and $181.4B costs in 2024. "Augment humans, not replace them" |
This is where Chris's head is right now. He is living the exact same phase you are: pre-revenue product, GTM being invented, hiring the first leaders. That symmetry is a gift for the conversation: you can ask how he is deciding pricing, first customers, and positioning at twelvesenses, and the advice flows back to SalesPros naturally.
The farm you're sleeping at
"The Battle Field Farm House by Octopus," Waterloo (yes, that battlefield). A historic property they renovated and opened around November 2025 as a hospitality venue for customers, partners, and Salesforce leadership: executive dinners, live demos, Bang & Olufsen-sponsored sound. The Donna voice-agent demo premiered over dinner there; Salesforce executives have visited for "dry runs." Expect a purpose-built setting for exactly the conversation you want, possibly with smart glasses and demo hardware within arm's reach. If they offer a demo, take it: reciprocity opens the door for showing SalesPros without it being a pitch.
Who else you might meet or hear about
- Ivo Costa. Chris's closest operating partner: co-founder/COO of twelvesenses, co-founder of the venture studio, "venture architect." Will NOT be at the farm; he reached out warmly on WhatsApp and you have a call with him next week. Full profile and the "work together" analysis in the Ex-Waeg network tab.
- Jens Vanden Meersschaut. Octopus Consulting co-founder, ex-Waeg, Diana's original MavenHive partner. Runs the consultancy with her day to day.
- Jan-Willem V. Belgian police chief inspector and founder of Learnr.be, the studio's first bet.
- Matthias de Bock. Was sales/marketing director at Octopus Consulting through the Donna era; now at Snowflake. May come up in stories.
Why this all matters for SalesPros
- Diana's firm is a live ICP sample. Senior-only Salesforce consultancy = the densest possible pocket of SalesPros users, and the Team plan was built for exactly that buyer shape.
- Chris chose product over services for his second act. He can speak first-hand to the services-vs-product question you'll face, and to selling into the Salesforce ecosystem from Europe.
- They already build with Claude + Agentforce. Your AI features and MCP/agent story will land with people who ship agentic Salesforce demos weekly. Complementary, not competitive: they bet on deskless voice/wearables, you serve the desk-side power user.
- Their whole playbook is relationship-led GTM: community events, demos over dinner, guerrilla marketing, a venue instead of an ad budget. Whatever advice you get will likely lean that way; it happens to suit a solo founder with a near-zero budget.
Links worth opening
People
- Chris on LinkedInSkim his last ~10 posts yourself; the voice and enthusiasm come through better than any summary.
- Diana on LinkedInRead the "get booed" entrepreneurship post and the executive-dinner recap.
Companies
- theoctopus.consulting10 minutes here pays off most: their positioning, the four offerings, the wearables demo. This is the company whose consultants are your ICP.
- twelvesenses.aiChris's current obsession. Know the Artificial Thalamus pitch before he explains it.
- octopusventure.studioShort read; note the founder-led intake language in case the topic ever arises.
- Octopus Consulting on LinkedIn · Venture Studio · twelvesensesCompany feeds; twelvesenses' is empty by design.
- learnr.beThe studio's first bet; good to know what it does if Jan-Willem comes up.
Waeg and the exit
- IBM press release, May 2021The official record, with Chris's quote.
- CX Today coverageContext: IBM's Salesforce acquisition spree (7Summits, Waeg).
- Waeg, an IBM CompanyWhat the brand looks like inside IBM today.
The wider network
Researched 24 Aug 2026 via LinkedIn (logged-in session). These are the people to reconnect with after the farm; Ivo's call is already scheduled for next week. When Chris asks "who should I connect you with," the first two names below are your answer. Full notes live in research-network.md.
Yves Van Looy warm · sales brain
| Now | Senior Advisor AI & Business at PwC (external/self-employed, since Jan 2025) · manager of his own Axxess BVBA |
| Waeg | Sep 2019 – Jan 2025: Director → Senior Director Delivery → Senior Sales Manager → Managing Director |
| Before | ~12 years Oracle (principal presales, then Benelux partner enablement) → Salesforce EMEA partner-practice development → managing partner at 7dots (Salesforce partner) |
| Activity | Sparse; mostly PwC reposts on AI-driven change, partner-led growth, EU AI Act, SAP transformation. Last original posts are 3–4 years old. |
The most senior pure-sales brain in your network, and he has sat on both sides of the Salesforce partner relationship (inside Salesforce doing partner enablement, and running partners). He can explain how a new tool gets adopted inside consultancies and what partner-led distribution actually requires.
Nick Celis warmest · fellow founder
| Now | Co-founder of Moss (workwithmoss.be), Apr 2026, Ghent: AI agents that take repetitive work out of company processes |
| Path | Waeg Business Partner CX (Oct 2021 – Jun 2024) → freelance CRM/data/AI at The Octopus Consulting (Jun–Nov 2024!) → Inkubis → Moss |
| Earlier | Co-founded IntoData 2015, grew it to ~25 people before exiting. This is his second founder run. |
| Moss traction | Several customers, workshops, go-lives; hired an AI software architect; brought in Maarten Laruelle to sharpen ICP and GTM; posts weekly about agent adoption, shadow AI, vendor lock-in, EU sovereignty |
Two things changed since you last looked. He is a founder again, four months into exactly your next phase (first customers, ICP, GTM), so he is living your problems in real time rather than remembering them. And he freelanced at The Octopus Consulting for half of 2024, so he knows Diana's shop from the inside and can give you an unvarnished read on the whole Octopus cluster.
Anup Jadhav long shot · AI + ecosystem
| Now | AI Product Lead at Oxford Dynamics (defence decision support), plus his own Inference Forge consultancy. London. 12k followers. |
| Salesforce | Nov 2020 – Apr 2025: Senior Program Architect → Director Solution Architect Program → Director Partner Delivery Success → Partner Alliances AI & Data Director. He has LEFT Salesforce. |
| Writes about | Production agent systems: single vs multi-agent design, "loop engineering," agent memory, cognitive debt from coding agents. Several original posts per month via anup.io. No recent Salesforce content. |
| SalesforceBen | Two old articles (2020, 2022); author bio stale; no visible current editorial relationship. A possibility, not a channel. |
The reconnection hook is better than expected, but it is not Salesforce. His current writing maps almost exactly onto how you built SalesPros: agent orchestration, when multi-agent beats single-agent, verification loops. Reconnect on AI engineering, where you have genuinely interesting field experience, and let Salesforce and SalesforceBen come up later if the conversation warms.
Ivo Costa call next week
| Now | Co-founder/COO twelvesenses (Mar 2026) · co-founder Octopus Venture Studio (Jan 2025) · Strategic Architect / Venture Builder / Board / People & Culture at Octopus Consulting · co-founder FoundersOhana · long-time mentor (The Mentoring Club) |
| Base | Lisbon (explains the Lisbon offices across the cluster) |
| Waeg | Jun 2020 – Sep 2024: L&D lead, then CHRO through the IBM integration. Your monthly-coffee near-friend from that era. |
| Recent signals | Shared the Octopus BD Director opening (Diana as contact); Sweden market-development mission with Chris incl. Salesforce Nordics leadership, "some conversations continuing"; wrote that the separate initiatives are becoming "a more structured system" to be connected and scaled together |
SalesPros: the facts you carry in
Everything here is source-verified against the repo (24 Aug 2026, master). Deeper detail: project-snapshot.md and product-tiers-and-discount.md.
State in one paragraph: feature-complete v1, far past typical MVP depth, entirely pre-launch: zero users, zero revenue. Chrome extension (SOQL editor, data loader, Apex, record tools, org compare, permissions, vault, AI), native Companion (real Apex LSP + MCP/CLI for agents), Excel add-in, Team plan, marketing site in coming-soon mode. Built solo in ~8 months at 20–30 h/week, ~1030 PRs, near-zero running costs. Committed: Chrome Web Store submission late September 2026. Remaining gates are days of checklist work: reviewer smoke + CWS submission, Companion re-release with the new pairing protocol, production billing end-to-end, email activation, site go-live.
Pricing and plans
| Plan | Monthly | Yearly | What it adds |
|---|---|---|---|
| Free | $0 | $0 | Core editors, completions (incl. picklist/record-type values), data loader, REST console, debug logs, unit tests. Metered in exactly four places: 10 vault credentials, 24h execution history, 1 active loader run, $me-only aliases. |
| Basic | $15 | $150 | Everything client-side: Apex LSP, advanced data loader (row editor, formulas, history), live reference search, record snapshots, compare/permissions tools, unlimited vault, BYOK AI. |
| Pro | $25 | $250 | Basic + cloud sync + managed AI + Companion agent channel (MCP) + Excel at $9 instead of $15. Nothing else separates Basic and Pro. |
| Team | $35/seat | $350/seat | Full Pro seats + shared team library. Closed at launch. No founding discount (separate checkout path). |
| Excel add-on | $15 ($9 w/ Pro) | $150 ($90) | Write-back to Salesforce from Excel; reads are free on any plan. Closed at launch. |
Managed AI caps: 30/day, 300/month per user, 1,000/day global, routed through OpenRouter only. BYOK capped at 500/day. Only 5 of 19 capabilities are server-enforced; the rest are honest-user UI gates.
Founding discount: what is actually true
- The promise in copy matches your intent already. Every instance says "50% off, locked in for as long as you stay subscribed." Nothing user-facing says "forever." If the sub lapses after the offer ends, list price applies. You can describe it at the farm exactly as you think of it.
- The kill switch is a Convex env var, not a PostHog flag. Unset STRIPE_COUPON_FOUNDING and new checkouts stop getting the discount; existing subscribers keep theirs (it lives on the Stripe subscription). Ending the offer is a paired action: env unset + a site deploy, because prices are baked into the site at build time.
- The discount DOES spill onto Excel added later (subscription-level coupon, deliberately unrestricted). This was an accepted tradeoff, but public copy claims the opposite in two places. Fix the copy before launch; the system undercharges vs its own promise, so the risk is inconsistency, not overcharging.
- Prod coupon validation has never run. It first executes when the purchasing flag opens at launch; a misconfigured live coupon closes purchasing for every SKU. Part of the billing E2E gate.
- Free's composer is less downgraded than the docs claim. Picklist values and bulk reference/record-type completions work on Free; only live typed-filter search and record search are Basic. Worth knowing before you describe the Free/paid line to Diana's consultants, and worth a deliberate decision: is Free currently too generous for conversion?
Market and competition
| Tool | CWS installs | Note |
|---|---|---|
| Salesforce Inspector Reloaded | 500k | Free, OSS, the mindshare default. Was 50k in Jul 2024 — 10x in two years, the strongest demand-growth proof you have. "A tool for nerds": powerful, but a utility, not a product. |
| Salesforce Inspector (original) | 100k | Unmaintained since Dec 2022, still installed everywhere. |
| ORGanizer | 80k listed (~90–100k per dev email) | The named paid comparable; PRO is $2.29/mo. Comparison page ships on the site. |
| Salesforce advanced Code searcher | 60k | Going stale (last update Nov 2024). |
| Salesforce DevTools | 50k | |
| Salesforce Logins (Synebo) | 40k |
CWS counts pulled live 2026-08-24; the store rounds down into bands (500k means 500–999k) and counts installs, not humans.
The optimistic read, which is also true: ~850k installs across the top eight tools — with heavy overlap, call it 400–600k unique practitioners — prove the audience exists, installs browser tools, and is reachable through the Chrome Web Store. You are upgrading a proven market, not creating one. A bottom-up cross-check lands in the same range: 150k+ customer orgs × 2–5 power-user seats = 300–750k. Wider funnel context, corrected after fact-checking: 170k+ certified professionals (a floor; no official count exists — the "~1M certified" figure is unsupported), 20M+ Trailblazer Community members (Salesforce's own wording; Trailhead usage itself is ~7M). The "~4M developers" figure is a 2016 AppExchange-installs stat — never cite it.
The sober read to keep private: at a 2–5% free-to-paid rate, the 350–400 payers you need (≈ €8–10k/mo, your quit threshold) imply roughly 10–20k active free users. That is the actual mountain, and it is a distribution mountain, not a product one.
Moat, in your own words
Salesforce will not ship this (the Dev Console has been neglected for 15 years; Inspector has existed for a decade without a Salesforce response). Agentforce is orthogonal: SalesPros is for people at the keyboard doing the work, and could even integrate Agentforce later. A volunteer OSS project cannot copy the surface area coherently: backend, sync, Companion, managed AI, Excel, team libraries all need someone whose job it is. Your unfair advantage: you are the ICP (10+ years Salesforce, 5 as architect on one org), you have breadth beyond Salesforce, and you demonstrably ship at a pace a side project cannot match.
The 60-second version
"I'm building SalesPros, a Chrome extension for people who live in Salesforce all day. Think Inspector Reloaded or ORGanizer, but built like a real professional product: an encrypted credential manager, a SOQL editor with actual schema-aware completions, a data loader that validates against the schema and lets you edit data in an Excel-like grid before you load it, Anonymous Apex with LSP support, permissions analysis and other admin tools. One extension instead of five. Plus two things nobody else has: a native companion that exposes SalesPros as MCP for agents and runs Salesforce's real Apex language server locally, and an Excel add-in with live Salesforce tables. I've been a Salesforce developer and architect for over ten years and built it because every existing tool made me settle for less. Free tier plus paid plans, submitting to Chrome Web Store in September."
Delivery notes: say it once out loud before the trip, then stop rehearsing. If a laptop is nearby, show the query-to-data-loader flow instead of describing it; the tool demos better than it describes.
The game plan
What you're there for: mentorship, ideally recurring; the Octopus pilot as your one ask; and answers on distribution, which is your real bottleneck. Not funding, not a pitch. You leave successful if three decisions change, not if thirty pages of notes exist.
If "work together" comes up
Ivo's WhatsApp message makes this likely. Chris and Diana probably know what he means; you don't yet. So decide the posture now, not at the dinner table:
- Warm, curious, unhurried. Something like: "Ivo hinted at that too. I'm genuinely interested, and I want to understand what it means concretely before I react. Let's not solve it over dinner."
- Questions that make it concrete: which company (Consulting, twelvesenses, the studio)? What problem am I solving in it? What role and time commitment? What economics? And the one that matters most: what happens to SalesPros's ownership and independence?
- Commit to nothing at the farm. Any real proposal survives a week of thinking. You have the Ivo call next week and a chat with Karolina today; both are your pressure-test loop.
- Remember your position: you have a well-paid job, no burn, no deadline, and a finished product. You need nothing from them urgently. That is negotiating strength; don't give it away by being flattered.
The 8-months question, owned
If asked why nothing has shipped in 8 months: it started as a tool for yourself, you're paid well enough not to rush monetization, and you chose to perfect it before releasing. One sentence of self-awareness helps: "Building was the comfortable part for me, which is exactly why I'm here before launch instead of after." Then the date: CWS submission late September. Don't apologize twice.
Spend most of the business time on distribution
Roughly 70% of whatever business conversation happens. Your funnel math (10–20k free users for 350–400 payers) is the honest framing of why.
For Chris
- How does a NEW tool get introduced to Salesforce professionals in Europe today? Which communities, events, and people actually move opinion?
- How do I get individual users to lobby their companies for the Team plan? Did anything like that ever happen inside Waeg?
- Is the AppExchange / Salesforce ISV partner route worth it for a browser extension, or a tarpit?
- He is inventing GTM for twelvesenses right now: how is HE choosing first customers, pricing, positioning? The advice flows back to you naturally.
- What would you stop doing tomorrow if you were me? (Then be quiet and let it land.)
- Who else from the old crew should I talk to? (Your candidates ready: Yves, Nick.)
For Diana
- Would your consultants use this over Inspector Reloaded? What would they mock, what would they love?
- Who signs a €10k/year tool spend at a 25-person consultancy, and how long does that take?
- What does a client of yours require before your people put a credential-vault extension on machines touching client orgs?
- What would make a free pilot actually get USED rather than installed and forgotten?
- She rebranded a company and does guerrilla marketing for sport: what would she do with zero audience and near-zero budget? On your weakest front, she may be the most useful brain in the room.
The one ask: the Octopus pilot
- Free Pro for anyone at Octopus who wants it, later Team when it opens. Delivered via a private sideload repo, so updates ship in minutes and skip the store entirely.
- In exchange: aggressive feedback and a shared Slack/Discord channel. Frame it as them getting a tool + shaping it; you get real senior users.
- Silently, this is also your Team-plan design partnership: adoption dynamics, security objections, procurement, whether $35/seat survives contact with a real consultancy. Ask pilot-shaped questions; don't announce the framing.
- Structural bonus: a pilot forces a follow-up conversation in a few weeks. That is your recurring-mentorship foot in the door without asking for a "cadence."
Answers to have loaded
- Who is it for? Salesforce professionals doing real work in the browser: pro-admins, consultants, testers, developers.
- Why pay when Inspector is free? One workflow story, not a feature tour: query with real completions → one click → schema-validated data loader → edit in an Excel-like grid → load. In Inspector that's three tools and a CSV in between. Then stop talking.
- What if Salesforce ships it / Agentforce eats it? They won't (15 years of Dev Console neglect); Agentforce is orthogonal and possibly integrable. Confident, short.
- What stops Inspector copying you? Coherence, pace, and the paid surface area (backend, sync, Companion, Excel, managed AI) that volunteer OSS structurally can't sustain.
- When do you launch? "Submitting to the Chrome Web Store late September." A date, not a sequence of gates.
- What would make you quit? Have an honest answer ready; "I've run 8 months on internal motivation alone" is a strength either way.
Running the 24 hours
- Don't front-load business. The good stuff arrives after dinner. Let the farm, Waterloo, CES, Waeg stories, and their demos run; Chris will ask about SalesPros when he's ready.
- If they demo (glasses, Donna), take it enthusiastically. Reciprocity opens the door for showing SalesPros without it being a pitch.
- Give Diana equal airtime. The trip is framed around Chris; the failure mode is Diana as bystander while she's the buyer AND the marketing brain.
- Interesting-person material, deployed naturally, never performed: the multi-machine multi-agent dev workflow (Chris runs an AI company; this is the thing in the room they can't easily buy); the embedded parking-device project (rhymes with their wearables bets); the Outlook→Google Calendar extension, pre-framed as a deliberate small-scope practice run of the full ship pipeline (built mid-SalesPros, never marketed on purpose).
- Write nothing during conversations beyond a phone note when something lands hard. Full brain-dump the morning after.
Leave with
- The pilot agreed in principle, with a named person to set it up with.
- A soft mentorship cadence: "can I write you a short update monthly and grab a call when something's decision-shaped?" is easier to accept than "will you mentor me."
- Two or three intros (Yves and Nick are your named candidates; let Chris add his own).
- Their honest read on the ladder (individuals → Excel → Team → enterprise) and the founding discount.
- The launch date said out loud, to someone whose opinion you care about.
What they may ask, and how to answer
Drafts, not scripts; say it your way. Items marked your input still need a real answer from you before the trip. Full version in qa-prep.md.
Warm-up
"How's the old client? Still there?" your input
Likely the literal first question. Five years on the engagement, three under Waeg, two after. Pick one concrete post-IBM story before the trip; nostalgia is your fastest rapport channel with Chris.
"Why did you reach out now?"
"I've been building something for eight months and I'm about to release it. The building part I can do. The business part is where I don't know what I don't know, and you're the person I most trust who's actually done this. I didn't expect a farm invitation, I was hoping for a coffee call."
"So what do you want from me?"
"Three things, honestly. Your read on my plan, because you'll see holes I can't. Some form of staying in touch, even just a short written update from me monthly and a call when something is decision-shaped. And if it makes sense after tonight, an introduction or two to people from the old crew."
For Diana separately: the pilot (see Talking points).
Product
"What is SalesPros?"
The 60-second pitch (SalesPros facts tab). If a laptop is in reach, offer to show instead.
"Why pay when Inspector is free and everyone has it?"
"Watch what happens when I write a query. Real schema-aware completions, results, then one click and I'm in a data loader that already validated everything against the schema, where I can edit the data in an Excel-like grid before loading. In Inspector that's three separate tools with a CSV export in the middle. And that's one of about six workflows like it. Inspector is a brilliant utility; this is a product."
"Show me."
Have the 3-minute path decided and rehearsed once: dev org logged in beforehand → composer completions → run query → handoff to loader → edit grid → validate. Backup moments: the vault, Apex LSP completions, MCP tools from a coding agent. Improvising a demo is how good tools look bad.
"What if Salesforce ships this?" / "Doesn't Agentforce eat it?"
"They won't, and the proof is fifteen years of the Developer Console. Inspector has existed for a decade without a Salesforce response; power-user tooling is simply not where they invest. Agentforce is orthogonal: my users are people at the keyboard doing the work, not delegating it. If anything I'd integrate Agentforce later, and Salesforce likes things that drive Agentforce usage."
They live in Agentforce world: dismiss the overlap, never the wave.
"What stops Inspector copying your best features?"
"Features, maybe. But not the coherent whole: the backend, sync, the Companion with a real language server, managed AI, Excel, team libraries. Sustaining that is a full-time job, and a volunteer OSS project has no incentive structure for it. I know exactly how much work it is because I did it."
"Why a Chrome extension?" example
"Because that's where the work happens: on top of the Salesforce UI, in the browser, all day. And where the browser is the wrong tool, I didn't force it: the Companion is native and the Excel add-in lives in Excel."
"Platform risk? Chrome could change the rules." example
"It's already Manifest V3, so the big purge is behind us. And the Companion, the Excel add-in, and the backend live outside the browser, so the product isn't one Chrome policy away from zero."
"Security and privacy? My consultants work on client orgs." (Diana; decides the pilot)
"Record data flows directly between the browser and Salesforce; my backend never sees it. Credentials are encrypted. Analytics are opt-in and EU-hosted, with retention crons that actually delete things. I wrote the Chrome Web Store privacy justifications the way I'd want to read them as an org admin. For a pilot I'd gladly walk your most paranoid consultant through the architecture."
Business
"Eight months and nobody's using it?"
Owned once, no apology spiral: started as a tool for yourself, well-paid job removed the rush, you wanted it excellent first. One line of self-awareness ("building was the comfortable part for me, which is exactly why I'm here before launch"), then immediately the date.
"When do you launch?"
"Submitting to the Chrome Web Store late September." A date, not a list of gates. If probed: reviewer smoke, billing end-to-end, email activation; days of checklist work.
"What's your pricing and how did you pick it?"
"Free tier, $15 Basic, $25 Pro, $35 team seats later. Anchored against ORGanizer's paid tier and what a professional tool is worth to someone who lives in it daily. Fifty-percent founding discount for early users, locked in for as long as they stay subscribed, claim window a few months. And the honest answer is nobody has ever paid, so pricing is a hypothesis, and it's one of the things I wanted your read on."
"How will people find it?"
"That's my weakest area and the main thing I want to learn from you two. Current plan: technical blog posts with the tool visible in GIFs, pushed through LinkedIn and the Salesforce community, plus a pilot with real consultants. The math says I need ten to twenty thousand free users for a few hundred paying, and I know a good product doesn't market itself. So: how would you two get a new tool in front of Salesforce people today?"
"What's the goal, lifestyle business or something bigger?"
"Honest version: a profitable business that lets me go full-time, which for me is around 350 to 400 paying users. That's the plan I control. I'm not chasing venture scale, but I'm not religious about it either; if it grows into something bigger, great."
You said you're comfortable sharing real income numbers with Chris; doing so builds trust.
"Would you take investment?"
"It wasn't on my radar before this trip, honestly. I'd consider it from people I trust, and you're on a very short list. But it's not why I came, and nothing forces it: I have income, near-zero costs, and time."
"You're doing this alone? What about a cofounder?" your input
"Alone, plus a small army of AI agents that do a lot of the building with me. I'm not looking for a cofounder right now; my gap is go-to-market knowledge, and I'd rather close that through people like you than by giving half the company to someone I haven't met yet."
Confirm: is "not looking" actually your position, even if the right non-technical person appeared?
"What happens when real users hit, at 20-30 hours a week?" (Diana will think of this)
"The support tooling already exists: an admin console, an iOS admin app with push, a log viewer users can export from. And the launch is staged on purpose: individuals first, teams later, enterprise when there's capacity. I'm not pretending I can support ten thousand users tomorrow; the plan doesn't need me to."
"Company setup? Taxes?" your input
Draft: "Being handled with professional help; not a launch blocker." Confirm what's true: entity status, and whether anything is genuinely unresolved before taking payments.
"What does it cost to run? What would money even buy?" your input
"Infra is near zero: Convex, Vercel, free-tier error tracking. The real spend is AI tooling, roughly [X] a month. Money wouldn't buy servers, it would buy my time, which is exactly why I'm not raising."
"What would make you stop?" your input
"There's no cliff; the pace is sustainable next to the job. But if a year of real marketing effort produced no conversion signal at all, I'd have to conclude the problem is the market, not the execution, and rethink."
"Where is this in three years?"
"The tool Salesforce professionals install by default, the way Inspector is today but paid and better. Me full-time on it. Maybe one or two people helping. The enterprise plan open. I'm deliberately not writing fiction beyond that."
Curveballs
"Ivo mentioned you two might work together."
"He hinted at that too, and I'm genuinely curious. I want to understand what it means concretely before I react: which company, what role, what happens to SalesPros. Let's not solve it over dinner."
"Would you ever sell it?" example
"I'm building it to be independent and profitable, not to flip it. But I watched you sell Waeg, so I won't pretend outcomes don't exist. It's just years too early for that conversation."
"What did building with AI agents actually change for you?"
Not a threat, a gift: the conversation Chris the AI founder wants to have. Have two or three concrete stories ready (orchestration across machines, what agents are genuinely bad at, the ~1030-PR number, review discipline).
"What's in it for Octopus?" (if the pilot lands transactionally)
"I'm not asking you to buy anything. Your consultants get a professional tool free and genuinely shape it: pilot feedback becomes features in days, not quarters, because there's no committee between you and me. If it makes them faster, everyone wins; if it doesn't, you've lost nothing and I've learned why."
Deeper inventory: the What I bring tab.
Things worth raising, with drafts
A menu, not a checklist: pick what the conversation invites; forcing any of these is worse than skipping all of them. Full version in talking-points.md.
Product moments (pick two or three; demo beats describe)
- The query-to-loader handoff. The best "oh, that's different" moment. "The thing I'm proudest of isn't a feature, it's that the tools connect. Query something, click once, and you're loading edited data back, schema-validated, without a CSV ever existing."
- The real Apex language server. "Every other tool fakes Apex intelligence with regexes. The Companion runs Salesforce's actual language server on your machine, so the completions are the real ones."
- The MCP agent channel. Their home turf. "Your coding agent can use my library too: saved queries and scripts over MCP, so Claude works with the same assets the human does. Read-only and save, never execute; agents shouldn't run Apex unsupervised."
- The vault and privacy posture. Diana's first objection, preempted. "Record data goes browser-to-Salesforce directly; my backend never sees it. Day-one design decision, because I knew the first question any consultancy would ask."
- Excel live tables. "Basically one serious competitor, and it costs more. Consultants live in Excel; this one's a sleeping asset I'll wake after launch."
- Release engineering maturity. Beta flags with a remote kill switch, retention crons, admin console + iOS admin app, telemetry wired. "It's run like a product company already; it just has zero customers so far. That part is deliberate and it ends in September."
The release story
- The date, said out loud. "Submitting to the Chrome Web Store late September." Saying it to people whose opinion you care about converts the perfectionism story into a commitment.
- The founding discount, then a question. 50% for early users, locked while subscribed, claim window the first months depending on growth. Then: "Would you cap it by time or by user count? Is fifty percent generous or desperate?"
- The ladder, offered for demolition. Individuals → Excel add-on → Team → enterprise. "That's my sequencing. Tell me where it's wrong." Between an ex-services-CEO who chose product and a consultancy CEO who buys tools, this collapses in one evening.
Distribution ideas to float
- The Octopus pilot (the one ask). Free Pro for anyone at Octopus, private sideload repo so fixes ship in minutes, shared feedback channel. Silently: the Team-plan design partnership (adoption, security review, procurement, whether $35/seat survives a real consultancy).
- The content engine. Technical blog posts with GIFs → LinkedIn + r/salesforce, on a schedule. Ask: which channels actually reach Salesforce professionals in Europe, and what would you cut?
- SalesforceBen. The biggest Salesforce blog runs a Chrome-extension comparison article; getting into it is a finite goal with massive reach. Raise as a question: "Do you know anyone there?"
- The ORGanizer migration path. Vault import already ships, comparison page is live. "Switching cost is the moat free tools hide behind, so I built an importer." Evidence you think about distribution, not just features.
- The community circuit. They sponsor summits and present at demo jams; Diana DJs at community parties. Soft: "Where should a tool like this show up?" If they offer to bring you somewhere, that beats any plan.
- The founding-user community. Slack/Discord for early adopters, feedback distance zero. Ask Diana whether early users actually join those or whether it's founder wishful thinking.
People and asks
- Intro list, ready when asked: Yves Van Looy (sales brain, partner-enablement history on both sides) and Nick Celis (fellow founder, four months into first-customers land, freelanced at Octopus in 2024). Ask Chris: "Who else from the old crew?" Ask Diana: "Who inside Octopus would actually champion the pilot?"
- The mentorship shape: not "will you mentor me" but "can I send you a short update monthly, and grab a call when something is decision-shaped?" Low cost to accept; the pilot creates its own follow-ups anyway.
Interesting-person material (rapport, not resume)
- The multi-agent workflow. Solo founder, seven surfaces, eight months at 20-30 h/week, ~1030 PRs, orchestrated AI agents across machines. Told as craft, with a story or two about where agents shine and fail. Possibly the most memorable topic of the night for an AI-startup CEO and CPO.
- The parking device. Own hardware for auto-starting parking from the car. Rhymes with their wearables bets; says "builds for the joy of it." One minute, with a grin.
- The calendar extension, pre-framed. "Mid-SalesPros I took a month to ship something small end to end, store review, billing, site, as a practice run. Almost no users because I never marketed it; the objective was the pipeline, not the product." Inoculated against the obvious follow-up.
Guardrails
- No funding ask; if money comes up, "I'd consider it from you specifically" is the whole move.
- Never ask what Waeg sold for.
- Don't force business talk; the overnight brings it to you.
- Diana gets equal airtime; on distribution she may be the more useful voice.
- Nothing "work together"-shaped gets agreed on-site, however good the wine.
- Leave with: three changed decisions, a pilot with a named owner, the date said out loud.
What I bring to the table
The other direction of the visit: why a relationship with you is valuable for them. Knowing this changes how you sit in the room, even if you never recite any of it. Source doc for iteration: value-to-octopus.md.
The honest baseline: SalesPros has zero users and zero revenue. What they get today is the artifact (a finished, deep v1), the person who built it, and the option value of being close to both before anyone else. What they can do for you is immediate; most of what you offer them compounds later. That asymmetry is normal, and it is exactly the trade a venture studio exists to make.
For Diana / Octopus Consulting
- Users in week one. 20–30 senior consultants living in SOQL, Apex, and data loads. The tool maps onto their offerings: audit/tech-debt practice ↔ org compare, permissions analysis, schema tools; implementation ↔ composer, data loader, Apex tools. The credential vault hits a specifically consulting-shaped pain (juggling client orgs daily). Free Pro is a small but real margin gain on billable time.
- Design partner leverage. The pilot molds the Team plan around how a real senior consultancy works, before any competitor has team features. Sideload distribution ships their feedback in minutes. Vendors don't listen to 25-seat shops; you will.
- Brand and content. "Our consultants helped shape the best professional tool in the ecosystem" is a sales line and a recruiting line for a senior-only firm. Diana does guerrilla marketing for sport; a tooling story is material she can play with.
- A channel, later. Clients ask consultancies "what tools do you use?" constantly. Octopus engagements seed users; SalesPros team leads inside client companies are warmer intros for Octopus. The loop exists without formalizing anything; affiliate/reseller is optionality for later.
For Chris / the studio / twelvesenses
- Proof of the thesis he's betting on. The cluster's bet is that small AI-augmented teams build what used to take companies. You are a completed, inspectable demonstration: one person, eight months at 20–30 h/week, ~1030 PRs, seven product surfaces, shipped through orchestrated agents. For a studio with a thin public story, a founder who already did the hard part is the cheapest credibility available.
- The method as transferable knowledge. The multi-machine, multi-agent workflow is scarce practical knowledge both Octopus Consulting and twelvesenses could use internally. Possibly the most immediately valuable thing in the room, independent of whether SalesPros succeeds.
- Salesforce depth where twelvesenses needs it. Thalamus names Salesforce as an event receiver. Ten-plus years of architecture plus working MCP/agent-channel experience is precisely their agentic lane.
- A founder who inverts their intake model. Their published entry point is concept-validation stage. You arrive with product proven and pricing built; only demand and distribution remain, which is their strongest suit. You already retired, at your own expense, the risk they normally absorb for equity.
- The Waeg dimension. An ex-Waeg architect shipping something excellent reflects on what Waeg was, and helping a Waeg alum ship is the story Chris already tells about himself (FoundersOhana, the studio, EO). Real motivation on his side; costs you nothing to let it work.
The brand, if associated
- "Octopus builds and backs products" gets stronger with a Salesforce-native shipping product in the story; none of their other bets are Salesforce-native.
- Farm-grade demo material: their guests are Salesforce executives and partners, and the query-to-data-loader flow lands in ninety seconds with anyone who has touched an org.
- Complementary, not overlapping: their bets are deskless/voice/wearables, you are the desk-side power user. Association widens their story without cannibalizing anything.
Value by relationship shape
| Shape | They get | You get | Main risk to you |
|---|---|---|---|
| Mentorship only | Chris does what he publicly loves, with a founder who ships | Guidance, intros, accountability | Essentially none |
| Pilot / design partner | Tool + influence over it; margin; brand story | Team-plan validation, senior feedback, recurring contact | Pilot scope creeping into free custom work |
| Channel / affiliate (later) | Product story, possible revenue share | Distribution into ICP | Complexity before product-market fit |
| Studio investment / incubation | De-risked Salesforce-native product + proven builder | Capital, GTM muscle, network | Ownership, control, independence: undefined until terms exist |
| Your time (delivery / twelvesenses) | Senior capacity they're constrained on | Income, closeness | The trap: consumes the hours SalesPros lives on |
If asked "why is this interesting for us?"
"Your consultants would use it tomorrow, and shaping it costs you nothing. Beyond the tool, I've spent a year learning how one person ships a whole product line with orchestrated AI agents, which is the same bet you're making across your ventures. And if it ever makes sense to go further together, you'd be starting from a finished product, not an idea."
Open questions, still iterating
- Where is the line between pilot feedback and free Octopus-specific feature work? Define "what serves all consultancies" before the pilot starts.
- If the studio conversation gets real: what would be worth giving up any independence for? Money alone isn't, while burn is near zero; distribution and selling muscle might be.
- Does association with one consultancy hurt neutrality with other consultancies, who are also ICP? Ask Diana directly; asking it shows you think in her categories.
Who she is professionally, current as of today
| Now | Director of Strategic Development at Everix Optical Filters (Orlando-based deeptech, since Jun 2023) · still an active Venture Partner at Eurazeo (since Sep 2023), focused on CEE sustainable-industry Series A/B · curator at Hello Tomorrow · Global Women in VC · Forbes 30 Under 30 |
| VC background | ICOS Capital 2020–2023 (associate → investment manager; Industry 4.0, agrifood, cleantech, deeptech), board observer at Invert Robotics, earlier ValueTech Seed Fund |
| Founder side | Co-founded medtech startup MEDIPRINTIC (2018–2021), so she has sat in your chair too |
| Everix | Ultra-thin optical filters, 34 patents, claims 10% of the Fortune 50 as customers; wearables, AR/VR, LiDAR, medical devices. She works international GTM for a deeptech operating company daily. |
| Recent | Posts from CES, Photonics West, Tokyo, Seoul, Brussels; spoke in Seoul on doing business in Europe vs US vs Korea; European Parliament event on the gender investment gap |
The useful fact: she is simultaneously an operator (Everix strategy) and an investor (Eurazeo venture partner). She can look at the farm situation from both sides of the table in one conversation, which is exactly what you need today.
What to ask her today
About tomorrow's conversation
- Here's my question list for Chris and Diana; which of these force a concrete answer and which let them stay in pleasant-anecdote mode? What's missing?
- What do technical founders in my position always get wrong in first mentor conversations? What should I NOT do?
- How do I ask for recurring mentorship without making it heavy? Does the "monthly written update + occasional call" shape work, or is there a better one?
About the "work together" signal
- Show her the Ivo exchange. From a VC seat: what is this, how do studios like this usually structure involvement, and what's the polite version of "name it concretely"?
- What facts and terms must I understand before agreeing to ANY venture-studio or operating relationship? (Ownership, IP, exclusivity, control, time commitment, what happens if it goes nowhere.)
- How do I keep warm optionality without drifting into an implicit commitment over dinners and calls?
About the plan itself
- Steelman the skeptic: if a founder brought her the ladder plan (individuals → Excel → Team → enterprise), the founding discount, and the TAM math, where would she poke first? Better to hear it from her today than discover it mid-conversation tomorrow.
- Her read on the quit math: 350–400 payers at ~€25 to replace a €11–12k/mo salary. Sane framing, or is she seeing a hidden assumption?
- Given her Europe/US/Asia GTM experience: anything structurally different about selling a prosumer dev tool from Poland into a global market that I should know early?
Market math to pressure-test with her (SAM / SOM / valuation)
Fact-checked 2026-08-24; the old top-down numbers (4M devs, 1M certified, 20M Trailhead) died in verification — see the SalesPros facts tab. This is the bottom-up version worth defending.
SAM — who can realistically install it
~600k people already install Salesforce Chrome extensions (~850k installs across the top eight tools, deduped for overlap; cross-checked by 150k+ orgs × 2–5 power seats = 300–750k). Theoretical ceiling if all of them knew SalesPros existed: 600k × 4% paid × $25 = $600k/mo = $7.2M ARR. A ceiling, not a plan.
SOM — what's obtainable in 2–3 years
Funnel, not a percentage of the market: 500k Inspector Reloaded audience × 10% try SalesPros × 4% convert (industry-standard freemium band is 2–5%) × $25 = 2,000 payers = $50k/mo = $600k ARR.
And the sentence that reframes the quit threshold: "My go-full-time threshold requires capturing about 2% of the audience Inspector has already proven exists, then converting at the industry-average rate." (2% of 500k = 10k triers × 4% = 400 payers = ~$10k/mo.)
Valuation, scenario-based (pre-revenue: no formula)
Pre-launch there is no defensible number; the honest line is "worth roughly nothing to a buyer and a lot to me, which is why I'm not raising pre-launch." Post-revenue, bootstrapped sub-$1M-ARR SaaS trades at 3–5x ARR in M&A; venture-context seed pricing (8–15x) applies only when raising with strong PMF.
| 12–18mo scenario | Payers | ARR (~$25/mo) | At 3–5x ARR |
|---|---|---|---|
| Slow | 150 | ~$45k | $135–225k |
| Base (quit threshold) | 400 | ~$120k | $360–600k |
| Strong | 1,000 | ~$300k | $0.9–1.5M |
What actually moves the multiple: growth rate, churn (3–6% monthly is normal for $25/mo prosumer SaaS), and NRR — above 120% earns 2–3x the multiple of below 100%, which is the valuation argument for the Team plan, not just the revenue one. At 4% monthly churn, lifetime ≈ 25 months, LTV ≈ $625, so any channel under ~$150–200 per subscriber works.
Pricing stance (for when she pokes at $25)
$25 is ~11x ORGanizer PRO ($2.29/mo) and above Copilot Pro ($10) and Raycast Pro ($8–10). Conscious choice: solo capacity meant slower initial growth was acceptable; after refinement, bug-fixing, and feedback the price can come down for a marketing push. Lowering is easy, raising is not. Ask her: does that sequencing hold from an investor seat, and is the 10% try-rate assumption in the SOM the weakest link?