You did it. You wrestled your startup from idea to reality, fueled by caffeine, conviction, and countless hours of founder-led sales. You were the sales engine. But now, growth demands more. You know you need to scale sales beyond yourself, and the immediate thought is often: “I need to hire a killer Head of Sales!”
Hold that thought.
While hiring great talent is crucial, jumping straight to recruiting a sales leader without laying the right groundwork is like trying to build a skyscraper starting on the 10th floor. It’s a common, expensive mistake that slows startups down.
As Lisa Calhoun, Managing Partner at Valor Ventures, shared in her recent Founder Masterclass, the transition from founder-led sales isn’t about finding one magical person. “Founders think they’ll find someone just like them, a relentless human being who’ll build it or bust down walls–but when you hire for sales, you’re not hiring another co-founder typically,” Lisa explains. “That person who is capable of selling no matter what is founding their own company.” Instead, it’s about methodically building your startup’s sales maturity – a spectrum of competencies, processes, and resources that set the stage so the proven sales leader you hire will succeed.
Think of it less like finding a needle in a haystack, and more like building a racetrack – creating the conditions where high-performance vehicles (your future sales team) can truly fly.
Valor uses a 10-step model to help founders assess their sales maturity–you can review it above.
Stages 1 & 2: Founder-Led & Early Sales Stage Discovery
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Stage 1 (Founder-Driven, Ad-Hoc): You, the founder, handle everything. Forecasts are gut feelings. Tracking is minimal. Every startup starts here.
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Stage 2 (CRM-Supported Discovery): Sales are still founder-led, but a CRM (even a simple one like Pipedrive) brings visibility. You start tracking deals, understanding time-to-close, and crucially, identifying patterns. Lisa notes the goal here: “understand what are the stages of successful sales, start to get a sense of the repeated questions, and what the successful customers have in common.” Obsess on that at this stage.
Stages 3 & 4: Building Structure & Support (Still Founder-Led)
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Stage 3 (Structured Pipeline & Basic Marketing): You refine pipeline stages based on successful deals that closed. Basic marketing materials (case studies, simple explainers) emerge. Use AI, and tools like Gamma.App or similar, to iterate quickly from your sales calls to needed materials.
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Forecasts become more data-informed.
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You get some support for scheduling demos from tools like Calendly.
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You might start templating some sales emails, or even use one of the off the shelf inbox support tools to help you crank out cold outbound like Fyxer–there are many. The point here is more about creating baseline resources for a process that can shorten the closing cycle.
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Stage 4 (Basic Sales Support & Predictability): You bring on appointment setters (SDRs) – not closers yet. Their job? Use your defined Ideal Customer Profile (ICP) and marketing materials to book qualified meetings for you.
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Daily check-ins refine the ICP and messaging. As Lisa emphasizes, “How many appointments can an appointment setter set a day? It will depend on rigorous clarity on who is a qualified lead.” Your sales will scale the fastest if you pick ONE type of customer–the ones who have the most pain, and the ability to buy in a reasonable time frame.
This stage is critical and often underestimated. As one founder realized during the workshop, “I think we want to jump from stage 1, 2 to stage maybe 5 or 6… maybe we are trying to jump these stages!” His co-founder agreed, “Yeah, that’s what we have been doing . . . And we have been trying to do it with junior people. So it’s even worse.” Lisa’s response was blunt but crucial: “Not gonna happen.” You can’t skip building the foundational understanding of your repeatable sales motion and expect to scale.
Stage 5: Scalable Infrastructure
This is where things get exciting. You have:
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Dedicated appointment setters hitting daily goals.
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A well-defined pipeline with stages and early conversion metrics from stage to stage (like, 80% of those who book a demo, take a demo. 70% of those who demo, buy).
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Regular sales meeting cadences daily, and early marketing support such as email templates, a sales deck, and some early case studies.
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Forecasts. As Lisa describes it, “Your forecast is accurate—like, it’s not a wish. It tends to happen, even as its also evolving and the product is evolving.”
You feel the pressure – you know you could grow faster with more closing power. Now you’re building an environment where a sales leader can thrive.
Stage 6: Hiring Your Professional Sales Leader
Because you’ve built the infrastructure (clear ICP, lead gen process, pipeline data, collateral), you can attract an experienced leader. They aren’t building from scratch; they’re stepping in to optimize and scale an early working system. “If you don’t have these things in place,” Lisa warns, “great salespeople will be like, ‘Yeah… I don’t know how I’m gonna be successful here.’ They’re looking for a place where honed skills in sales are needed, not skills in building infrastructure primarily.”
Stages 7-10: Scaling, Optimizing, and Autonomy
These later stages involve expanding the team, integrating AI thoughtfully (for onboarding, support, augmentation), refining operations, potentially bringing in operational leadership (COO/CFO), professionalizing systems (like migrating to Salesforce), and establishing a fully accountable, high-performance sales organization where the founder focuses primarily on strategy and top-tier relationships.
The Takeaway: Build the Racetrack Before Hiring the Racecar Driver
Founders often ask, like one founder did in the last Masterclass, about taking deals outside the core ICP when revenue is needed. Lisa’s advice is key: the founder, with their inherent authority, can make strategic exceptions. But the system and the team you build need discipline. “You put them [sales hires] in a terrible position… if they have to come back to you to get permission to do something weird. Focus them on a cadence that delivers success–it’s only the founders who can make the judgement call of selling ‘off book’ otherwise you interrupt things like your forecasting clarity, and your commitment to an ICP.” Selling a unique deal after a unique deal is also a great way to over-build your product, potentially even for the wrong ICP.
Scaling sales effectively isn’t about finding one superhero hire.
It’s about a disciplined, staged approach to building your sales infrastructure and talent together.
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Assess: Honestly evaluate where you are on the 1-10 maturity scale.
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Focus: Identify the next logical step to strengthen your foundation. Is it implementing a CRM? Refining your ICP? Documenting your sales stages? Building basic marketing collateral? Hiring appointment setters?
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Build: Execute that next step. Treat building your sales process like building your product – iterate, learn, and systematize.
By focusing on this holistic infrastructure first, you create a stable, predictable, and ultimately faster-growing sales engine. You make your startup far more attractive to top sales talent because you’re offering them a well-paved racetrack, not asking them to build it while driving. The results – and the right hires – will follow your leadership in setting the pace.