Founder-Led Sales to Repeatable GTM
Fractional and Interim CRO for technical founders at Seed–Series B. I narrow ICP, build pipeline from zero, and personally close the founding enterprise deals — then coach the team you hire next.
Book a 30-min call →$100M+
Personally Closed
$1B+
Team Revenue
25+
Years B2B SaaS
Most Seed–Series B startups don’t fail on product.
They fail because founder-led selling stalls before a repeatable revenue engine is in place.
ICP is fuzzy. Messaging hasn’t converted. Pricing is a guess. The next $250K of ARR depends on the CEO’s calendar.
Hiring an SDR doesn’t fix it. Hiring a $400K VP Sales too early breaks it.
The technical product is great. The technical founder is brilliant. The revenue motion is improvised. And the company stalls.
Sound familiar?
What a stalled revenue engine looks like from the inside.
- The founder is still on every deal that matters, and the second seller cannot close what the founder closes.
- The pipeline looks full and deals stall at the same stage every quarter.
- The forecast is a list of hopes; the quarter ends in a scramble and a surprise.
- Sellers give different answers to “why do customers buy from us?”
- You have hired reps and added cost without adding capacity.
- AI agents are already prospecting, enriching and forecasting in the sales org, and nobody can say what they are allowed to do.
Stage fit
Where you are, what is broken, what I do.
Founder-led selling has stopped scaling
The problem: only the founder can close, and the ICP, positioning and process live in their head. What I do: write the ICP with disqualifiers, close the founding enterprise deals personally, turn what worked into the playbook, and hire the first reps against it. Stages 01–04 of the Revenue Foundation.
Pipeline is growing; win rate, velocity and forecast accuracy are falling
The problem: activity without a system — no exit criteria, no qualification discipline, no forecast anyone signs. What I do: rebuild pipeline architecture, install discovery and MEDDIC qualification, and stand up the weekly cadence and the board reporting. Stages 03 and 05.
Moving from SMB or self-serve to enterprise without the motion for it
The problem: enterprise buyers ask security, authority, procurement and evidence questions the current pitch and price cannot answer. What I do: redesign positioning and pricing for the enterprise buyer, rebuild discovery for the longer cycle, and run the first enterprise deals to signature. Stages 02–04.
A sales leader has left, or the board wants a different answer
The problem: the seat is empty at exactly the wrong moment, and a rushed permanent hire is the expensive way to run a diagnosis. What I do: hold the seat as Interim CRO for a defined term, stabilize the forecast, and write the job description from inside the seat so the permanent hire is the right one.
Embedded operator. Player-coach. Builder.
Six areas of focused work — every engagement, every founder.
Product-Market Fit & ICP
Customer discovery sprints, ICP refinement, win/loss analysis, positioning and messaging that converts pain into urgency, pricing and packaging hypotheses.
Pipeline From Zero
Trigger-event targeting, modern outbound stack, agentic workflows for outreach and qualification, multi-threaded prospecting into CIO, CTO, Security, and Procurement.
Full-Cycle Closing
Founders’ first deals: discovery, demos, POCs, security review, procurement, negotiation. MEDDIC discipline. Mutual action plans. Champion development.
Technical Fluency
Credible with engineering CIOs and CTOs. Across AWS, Azure, GCP, OCI. AI governance, agentic GTM tooling, Infrastructure-as-Code.
Leadership & Team Coaching
Hiring scorecards, AE/CSM onboarding, deal-review cadence, 1:1 coaching, founder-to-CEO transition support. Built teams from first AE to 20+ across direct, partner, and channel.
Operating Foundation
CRM workflows, forecast cadence, dashboards, board-ready revenue metrics — so the next hire inherits a system, not a hero story.
25 years of building B2B SaaS revenue.
- $100M+ personally closed in B2B SaaS across AI, cloud infrastructure, cybersecurity, and FinTech.
- $1B+ in revenue delivered by GTM teams I’ve built and led across direct, channel, and partner motions.
- Microsoft Partner of the Year — Business Transformation, leading global alliances and channel ecosystem at Aisera.
- Founder / CRO, Investor Services: scaled platform from concept to 2M+ accounts and $15B+ in assets (Acorns, Charles Schwab, LendingClub, Wealthfront).
- CoS / CRO, FluidCloud: building hyperscaler marketplace motion for an IaC platform spanning AWS, Azure, GCP, OCI, VMware, Nutanix.
- Fortune 1000 customers include Amazon, Microsoft, IBM, Oracle, Bank of America, Wells Fargo, Cisco, Intel, Dell, Boeing, Disney, Walmart, Sony, HP, Lockheed Martin — plus 50+ Fortune 1000 customers and partners across 15+ industries.
50+
Fortune 1000
Customers & Partners
15+
Industries
Represented
100+
Strategic Enterprise
Accounts
$1B+
Revenue Impact
Generated
25+
Years Building
Revenue Teams
Worked examples
Three builds, three stages.
What the Revenue Foundation looks like once it is built — in three companies where I built it.
Idea to a running company
The founding ICP, the customer-discovery framework and the MEDDIC qualification discipline — the first repeatable playbook the company could hire against — then the KPI-driven revenue operating cadence, for an enterprise Infrastructure-as-Code platform spanning AWS, Azure, GCP, OCI, VMware and Nutanix, taken to market through the hyperscaler marketplaces.
The founding customers, then the engine
From the company’s earliest days: the founding customers closed personally, then the repeatable sales engine that carried the company to 100+ enterprise customers, $42M+ in revenue and its acquisition by Oracle.
Concept to a platform others build on
A venture-backed FinTech and WealthTech platform scaled from concept to 2M+ accounts and $15B+ in assets under custody, with Acorns, Charles Schwab, LendingClub and Wealthfront on the customer list.
Who I work with.
You’re a fit if:
- You’re a Seed through Series B technical founder, zero to $10M ARR
- Enterprise B2B with CIO, CTO, Security, or Procurement buyers
- AI, cloud infrastructure, cybersecurity, FinTech, dev tools, data
- You’re still personally closing the founding deals
- You know a $400K VP Sales hire is six months too early
I’m probably not a fit if:
- You’re a PLG or SMB-only motion with no enterprise tier
- You’ve already passed $10M ARR with a full GTM team
- You need a part-time consultant who advises but doesn’t execute
- You’re looking for someone to attend strategy meetings, not close deals
Not a lead-generation agency. Not an outsourced SDR team. Not a slide-deck consultant.
A fractional CRO is an executive operator with a seat at the leadership table and a number attached to their name. If the ask is really “fill the top of the funnel”, an agency is cheaper — and I will say so. What the job actually is »
The part nobody else scores
The revenue engine now has agents in it.
Prospecting, enrichment, call notes, forecasting — the sales organization is adopting AI agents faster than any other function, and boards are being shown numbers nobody can verify. I bring the governance and measurement discipline as part of the operating system, not as a separate project.
The Agent Inventory
Every agent in the revenue org, eleven fields each, as the system of record for what they may do.
Read »Write the Mandate
A one-page delegation of authority for each agent that touches customer data or spend.
Read »The Three Measures
Inputs, outcomes, organization — the scorecard that survives the J-curve, for your AI and your customers’.
Read »What changes when the company sells AI
Outcome pricing, a new discovery question, and a J-curve in the customer’s P&L.
Read »Questions founders usually ask first.
What does a typical engagement look like?
2–5 days/week, 3–6 month minimum, fractional and equity-aligned. I sit beside you as an embedded operator — defining ICP, building the first repeatable playbook, personally carrying a bag on the founding deals, and coaching the team you hire next.
How is this different from advising?
I do the work, not just diagnose it. I personally run discovery calls, sit in the demos, walk procurement through redlines, and write the security review responses. The founder watches, participates where it matters, and reclaims calendar capacity to focus on product.
What sectors do you have deepest experience in?
AI and agentic GTM tooling, cloud infrastructure (AWS, Azure, GCP, OCI), cybersecurity, FinTech, dev tools, and Infrastructure-as-Code. Fortune 1000 customer history spans 15+ industries from financial services to defense.
What about pricing?
Engagements are structured to fit the stage — typically a base monthly retainer plus equity participation, calibrated to your funding runway and ARR target. Happy to discuss specifics on a discovery call.
How quickly can we start?
Typically within 2–3 weeks of a discovery call, depending on capacity. The first 30 days are customer discovery; weeks 5–12 are pipeline buildout and active selling.
Also a fit
Three situations I take on beyond founder-led.
The board wants forecast confidence and a value-creation plan the commercial team can execute
Board-ready cadence, pipeline truth, pricing and packaging, and the enterprise deal discipline that moves the multiple.
How I work »The Series A or B is closed and the commercial system has not caught up with the headcount plan
The ICP, the playbook, the hiring scorecards and the cadence, installed before the new reps arrive rather than after.
The first thirty days »A leadership gap, a reset, or a pre-transaction period
The seat held for a defined term at an agreed number of days a week, with the search for the permanent leader built into the plan.
Fractional vs. interim »The facts a founder needs before the first call.
Stage, buyer, motion, contract size, scope, and terms — so you can tell in five minutes whether I’m the right operator for your company.
Writing worth your time.
The thinking behind the work — frameworks and field notes from 25+ years building enterprise revenue.
Framework
The Seven C’s of Selling
A deal-dynamics model for enterprise sales — the seven forces that decide whether a complex deal closes, and when. Read →
Essay
Founders Don’t Fail on Product
Why most Seed–Series B startups stall on the chasm between founder-led selling and a repeatable revenue motion. Read →
Crossing the chasm?
If you’re a Seed through Series B founder navigating the gap between founder-led selling and a repeatable revenue engine, I’d be glad to spend thirty minutes.
Book a 30-min call → todd@yancey.com • +1 (650) 572-5000 • linkedin.com/in/toddyancey