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Patrick sat down with Monica Stewart, a longtime go-to-market operator who’s spent her career helping small teams sell into very big companies. Monica’s done the quota-carrying grind, built enterprise motions inside startups, led revenue transformation work at Scale(d), and for the past several years has run MSP Consulting—working with founders (typically around Series A and B) who have early traction and want to scale without breaking what made sales work in the first place.
This conversation is a reality check for the “we found product-market fit, now we just hire AEs and grow” storyline. Monica’s take is that scaling revenue isn’t a single gate you pass through. It’s a series of mindset shifts, system upgrades, and uncomfortable tradeoffs—especially for founders who want to get out of sales as quickly as possible.
Early on, Monica pushes back on a belief you still hear constantly: that you need deep industry experience to sell effectively. Her career is basically the counterexample. She’s sold to procurement and supply chain leaders at Fortune 500s, and she’s sold to small multifamily real estate investors. She’s worked inside companies that were never more than ~100 employees, yet consistently sold into the biggest organizations in the world.
What she’s really describing is the difference between understanding an industry and understanding how buyers and organizations make decisions. The surprise (once you’ve lived it) is that enterprise deals are often less about the product details and more about the “organizational personality” of the company you’re selling into. Certain companies tend to buy early. Certain ones move slowly but predictably. Some have cultures where consensus is everything, while others let a single strong operator run the show.
That’s why variety can be an advantage. When you’ve sold across markets, you stop believing in one universal playbook. You get faster at spotting the real pattern: the buying motion, the internal decision dynamics, and how people behave when the stakes are high. In Monica’s world, learning that “company personality” is often more valuable than memorizing jargon.
Monica’s path into sales starts where a lot of good sellers begin: with a degree that teaches you how to argue persuasively. She studied political science and international relations, and she makes the point that sales is basically the same muscle. You learn the history, build a narrative, and your success depends on how well you defend it.
Her first sales job also shaped her philosophy in a way a lot of founders underestimate. She was 22, making 100 cold calls a day starting at 7 a.m. because she was selling into European institutional investors. The people she was calling ran trillions of euros, came from elite backgrounds, and had no interest in small talk. Monica didn’t have the option to “sound smart.” She didn’t have industry credibility to lean on. She had to learn how to talk to people by being genuinely interested, not performatively interesting.
That’s also why her favorite early advice is so memorable: don’t try to impress anyone—because you can’t. If you stop trying to impress, you ask more questions. And if you ask more questions, you actually learn what’s going on. That shift sounds simple, but it’s foundational—especially in enterprise sales, where buyers can smell “I’m trying to prove I belong in the room” from a mile away.
It also ties into something Patrick mentions later: listening to understand, not listening to answer. The moment you stop rehearsing your next smart-sounding line, your follow-ups get better, your discovery goes deeper, and your whole deal motion becomes more real.
Monica works with founders who usually aren’t “idea stage” early. They’ve got real revenue, often $1M+ ARR, and they’ve been selling long enough to know what’s random luck versus repeatable motion. But she’s also careful not to define PMF as “hit a revenue number and you’re done.”
In practice, she’s looking for a few signals:
She wants you to be able to describe your customer with specificity—who buys, why they buy, and what changes for them. She wants some form of repeatable top-of-funnel channel, even if it’s scrappy: referrals you can trigger, conferences that reliably generate conversations, clear ecosystems where your buyers hang out. “It was super random” isn’t a strategy.
And she’s big on adoption and retention. Revenue can be misleading—especially in businesses with huge deal sizes where a handful of customers can inflate the number. The real tell is whether customers stick, expand, and actually use what you sold them.
But the most important part of her definition comes later: she believes your understanding of PMF should be updated regularly. Hitting early PMF is like hitting an MVP version of truth. The market keeps moving. Your best-fit segment becomes clearer. Your “ideal customer” evolves as you gain more data. So for Monica, PMF isn’t a milestone—it’s a hypothesis you revisit at least a couple times a year.
When Monica talks about post-PMF scaling, she goes straight to the uncomfortable thing founders don’t want to hear: the biggest problem is usually mindset.
A lot of founders mentally skip the messy middle between “I can sell this” and “a team can sell this.” They assume the jump is straightforward: hire an AE, hand them your sequence, and watch revenue multiply. But in reality, the $1–3M range is often founder-led sales plus early hustle. Go-to-market fit isn’t proven when you personally can close deals—it’s proven when you can onboard, support, and retain a team that consistently hits goals.
Monica frames it in a way that’ll land for product-minded founders: if your sales team are your users and your go-to-market is the product, you don’t have GTM fit until your users are succeeding and sticking around. Founder-led sales can be an early sign of “this works,” but it doesn’t mean the system is transferable.
This is also where she’s blunt about founder involvement. In complex enterprise sales, stepping out too early is a mistake. Even if you’re still “running a few deals,” you might not be supporting the bulk of what the team is trying to close. Monica’s ideal is almost funny: you should be involved so deeply that your reps eventually tell you to get off their calls because they’ve got it. Until you reach that level of confidence and capability in the team, most founders are pulling away too soon—usually because they’re tired of selling, or because they want to go back to product.
And there’s a second-order effect founders miss: selling keeps you close to the market. When technical founders reduce their sales involvement, they often distance themselves from real customer truth. Even after $1–3M, your product still needs to evolve, and sales conversations—especially renewals—are where you learn what’s changing.
The second major scaling challenge Monica calls out is founders clinging to the early playbook. A sequence that “worked great” two years ago is rarely still effective today. Deliverability changes. Buyer attention changes. Tactics get copied, abused, and diluted.
She’s candid about why: in sales, we can’t have nice things. The moment something works, people copy it badly at scale, and the tactic gets burned. So the requirement isn’t to find one magic button and press it forever. The requirement is to keep reinventing—new channels, new messaging, new approaches, new tools.
Monica’s operating expectation is simple: you should be reviewing your campaigns at least monthly, asking whether the current conversion rates and volume actually get you to the goals. And the answer, in her experience, is usually not “add more volume.” It’s improve conversion.
Patrick echoes a version of the same point from the Pod lens: a lot of companies think they have a top-of-funnel problem, but they’re leaving half their leads untouched for two weeks and failing to move deals stage-to-stage. They’re buying attention and then wasting it. Monica extends it into a flywheel: when you improve conversion, you get better market insight, which makes your top-of-funnel targeting smarter, which further improves conversion. But if you neglect discovery and don’t capture meaningful information, you handicap both ends of the funnel.
One of the most practical sections of the conversation is Monica’s take on staffing. Founders often want to hire a senior sales leader early, but Monica sees that create forced, expensive growth: you hire someone pricey, and their first instinct is to hire more people. Suddenly you have a larger burn, a bigger quota stack, and not enough demand to support it.
Her preferred pattern is more conservative and often healthier: keep hiring individual contributors until you have about four or five, and then layer in a sales leader to manage and scale the system. Until then, the founder needs a vision for how they’ll operate as a sales manager—because the team will need support, not because they’re incompetent, but because the job requires management. Even the most “independent” seller becomes more successful with better resources, clearer process, and real coaching.
That idea connects to another subtle theme: sales has a deceptively low barrier to entry. Anyone can technically “do sales” if they have a phone and email. But doing it well—building process, running discovery, coaching, designing a repeatable motion—is a different level entirely. Monica loves working with founders who recognize that gap. They’ve read books, listened to podcasts, tried things, and still know there’s a layer they haven’t personally done before.
When Patrick asks for non-people levers—process, tools, systems—Monica goes straight to conversational intelligence. She’s emphatic that early-stage teams should use a tool built for sales, with strong CRM integrations and models designed around sales workflows. In her view, dumping raw Zoom transcripts into a generic LLM can save admin time, but it won’t reliably generate coaching insight, pipeline patterns, or process improvement unless you supply a ton of context yourself.
The real value isn’t summarizing one call. It’s understanding patterns across calls, across accounts, and across stages—then feeding those insights back into qualification, discovery, messaging, and coaching. That’s where conversational intelligence becomes an actual scaling lever rather than a note-taking convenience.
In the closing rapid-fire, Monica makes three points worth sitting with.
First, her favorite framework is MEDDIC—but with a crucial caveat: it’s a qualification framework, not a discovery script. Used behind the scenes, it helps teams separate real deals from non-deals faster than anything she’s seen.
Second, she strongly disagrees with the classic “find the pain and amplify it” approach. She calls it outdated and based on information asymmetry that doesn’t exist anymore. Sophisticated buyers know what’s wrong. They have reasons for how they operate. If you try to win by making them feel bad about their choices—or trashing the incumbent vendor they’ve worked with for years—it backfires. Her preferred reframe is respectful and forward-looking: what you have worked to get you here, but where you’re going is different, and you’ll need different tools for that future.
Third, the most undervalued late-career sales skill is storytelling. Not the fluffy kind—the enterprise kind. Monica argues that ROI decks fall flat when they’re just a pile of numbers that imply the buyer is foolish not to buy. The better approach starts with where the customer is today, maps the path to where they want to go, and positions your product as the tools that help them make that transition. The metrics support the story; they aren’t the story.
Patrick adds an important angle: storytelling helps the buyer too. Many buyers don’t fully grasp their own narrative because they’re buried in day-to-day chaos. A great seller runs discovery like a diagnostic, then plays back a clearer version of the buyer’s situation—almost like a therapist giving full attention and reflecting back what they’re hearing. In larger, longer deal cycles, skipping that work can actively jeopardize the deal.
Monica closes by pointing people to where she shares these perspectives most consistently: LinkedIn, where she posts almost daily.
If you’re a founder staring down the $1–10M climb, her message is clear: you don’t “graduate” from sales. You evolve it. And the companies that scale aren’t the ones that find a playbook once—they’re the ones willing to keep rewriting it.
