Selling the Mario-on-Blast: Jen Abel's Playbook for Growing Enterprise Sales from $1M to $10M ARR

Jen Abel, who co-founded the sales consultancy Jellyfish and now runs enterprise at State Affairs, opens with her most contrarian claim. Ask ten people to define "enterprise" and you will get ten answers based on revenue, market cap or headcount. In her view, selling to a 100-person company is a radically different game from selling to a 1,000-person company, and there is no hybrid approach in between.

Her simplification is to sort everything into two silos. Small business is typically powered by marketing, while enterprise is typically sales-led. When someone says they are targeting the mid-market, she asks whether they mean the upper end of small business or the lower end of enterprise, and most people mean the latter.

Once you know you are playing the enterprise game, she says, you know which people to hire and what contract size they need to chase. Mixing the two approaches is where companies lose, because they are so distinctly different. She points to a chart showing that the number of companies drops off along a power law, so very few firms really sit in the middle.

Conventional advice tells startups to avoid the Walmarts and Exxons and learn on smaller, faster customers. Abel says the opposite. Number-one companies have to keep taking swings to stay number one, so a leader who gets even a small edge from your product earns a promotion and a pat on the back.

Those buyers also want a voice in your roadmap. It is still the founder's job to decide what gets built, but a tier-one customer's input can take you from a $100,000 deal to a million-dollar one in a short time. In the age of AI, she argues, the goal is to get your foot in the door at the enterprise before someone else does.

By tier one she means companies like Walmart, McDonald's, Nvidia, Tesla, Exxon Mobil and United Healthcare, the leaders in their space. Landing one is, in her words, "all the proof you need," and it also excites investors, future employees and the number two to four players who want to copy the leader. Later in the conversation she adds that these firms attract the strongest talent, which creates a compounding effect.

To reach a Walmart-sized target, Abel says the first step is to get the founder involved, since everyone likes talking to a founder. The second is to sell to a gap rather than a problem. Problem selling is specific, technical and what every trained salesperson does: find the problem and anchor to it.

When selling to a leader, you should instead sell an opportunity, the way the well-known meme says to sell "Mario on blast" rather than the mushroom. She describes this as offering alpha: access to information, data or a way of working that gets the customer further upstream than anyone else. She compares it to high-frequency traders buying one second of advantage, which is not pitched as fiber connectivity.

Abel notes that the image traces back to Kathy Sierra's idea of making users into superheroes. Founders sell well because they gravitate naturally to vision, while a scripted salesperson's discovery questions can kill the vibe. When Lenny asks how a Cursor rep might do this, she suggests pitching access to 10x engineers who want to use the tool, rather than simple productivity.

Abel's colleague Justin says most founders would rather land ten $10K deals than lose nine and win one $100K deal. She says early on people discount "till the cows come home," but the best clients will not nickel-and-dime you. If they do, they aren't fully bought in. A single "rockstar" client who helps shape the next stage is worth more to her than ten or so customers, half of whom are a poor fit but still need service.

Enterprises make buying hard on purpose, she says, so that only things they really want get through. A champion goes to bat maybe once every two or three years, so the purchase has to make them look like a superhero. A $100K deal also forces an executive to sign off, which means you know they are bought in even if it takes two more months.

On pricing for venture-backed companies she is blunt: you cannot sell $10,000 deals to the enterprise and expect the math to work. A strong salesperson will also want commission on a $250,000 or half-million-dollar deal. The one exception she gives is when a small first contract quickly steps up, for example from $10K to $50K within months.

The risk of the small deal is the anchor. If you sell three seats to Walmart at small-business pricing, the price is documented, and a buyer will ask what the 10x step change in value is when you later ask for $90,000. She suggests landing somewhere between $75K and $150K, keeping the scope contained, and planting the seed for years two and three. Even a land-and-expand story only works if the jump is defensible, and she says you need to show something like 15x value.

Abel loves design partners but warns that they are the hardest logos to upsell into full rollout customers, so don't expect them to become your million-dollar pipeline. She likes technology-minded Fortune 1000 companies that are used to experimenting, since they understand a janky early product. Converting one into a full customer is, in her view, a huge win for the team and for investors.

The trick is to set the framing from the start: ask them for some skin in the game, and tell them where pricing is headed. She gives the example of offering a design partner a permanent 30% concession for being there on day one, while still defining the eventual price. Just as important is picking the right person, someone who is excited to give feedback and aligned with the founder's view of the world.

Abel says salespeople often oversell design partners, which leads to churn and frustration, so she recommends being explicit about what the product cannot do yet. On whether a partner can pull you off course, she says the founder's job is to hold a clear vision and interpret feedback, since much of it reflects the old way of working. She recalls one founder who treated roughly 80% of the feedback as noise, but the other 20% drove everything.

On whether to go enterprise or SMB at all, Abel says it comes down to which game the founder understands best. A founder who is an incredible marketer with a way to win a massive audience should go SMB, while one who understands how large corporations work and is excited by $100K-plus deals should go enterprise. She also notes that selling to enterprises can be easier when you do not need to touch their data at the start, which she suggests was part of how OpenAI got in.

She argues that early-stage enterprise sales is more art than science. Deal crafting means making the value feel far larger than the cost, partly by giving away things that cost you little but would be expensive for the customer, such as building an integration over the next year or inviting them to speak at your event. In her words, the product includes pricing, framing and the opportunity, and once you become one of three options being compared you have "already sort of lost."

Her other surprising piece of advice is to start by selling services even if technology powers them behind the scenes. Enterprises spend their largest budgets on consultants and external resources, so services are what they know how to buy. After you are in, you guide them toward the product that was doing the work all along. She compares this to forward-deployed engineers at Palantir and to consultancies like McKinsey sitting in client offices.

She is skeptical of channel partnerships, though. With a hundred startups on a Deloitte or Accenture list, she says, you are counting on consultants to sell on your behalf, and they are not vision casters.

From $1M to $10M, Abel says, the founder can no longer carry every deal, and you need strong enterprise sellers who understand how corporations buy, how executives think and how much risk they can tolerate. Hiring a small-business rep, or a very junior one, and expecting them to convert executives rarely works. She wants people who can "cosplay the founder": sell the vision, run through walls and get creative, since none of her deals look the same.

Her ideal profiles are a former founder, or someone with no sales background but deep product or engineering experience. Typical salespeople often feel salesy, and she notes that the market doesn't want to be sold to; it wants to buy. She also cautions against a VP of sales from a big company because their old brand did the trust-building, and at this stage the product is still new.

Rather than counting years of experience, she looks at whether you would want to buy from this person and whether they mirror the market they sell to. On motivation, her answer is incentives: salespeople love to make money. She says compensation is usually 50% base and 50% variable, with commission of roughly 8 to 12% in technology.

She suggests hiring the first rep around $1M ARR, once you have seven to 10 customers and a pattern to share. Have the founder join the first five calls, and expect to fire about one in every two salespeople. Recalling advice from Jason Lemkin, she agrees that hiring two at a time makes sense so you can compare them.

For getting a first meeting, Abel says the vision is what gets a call. Keep the message to about three sentences, say something counterintuitive, and make it feel like the recipient can learn something in 15 minutes. She also says that if your deal is $5,000 you need a marketing-led engine, while a $100K deal means outbound from day one.

She says every enterprise deal she has closed was done largely over text, because it is a relationship in which she picks up when the client calls. That trust makes people "turn over rocks" for you, such as a Fortune 10 contact who agreed to try to get a deal done in the year. She also co-authors pricing with the buyer, giving them something they can take to their own leadership, and might trade a lower price for a longer lock-in.

She asks the questions people are afraid to ask, such as whether a deal will really close this year, and treats a quick "no" as valuable data. If she senses someone is only being polite, she says so on the call, and the answer saves everyone time. Her goal is to qualify on the first call.

Abel uses no outbound tool. She writes each note by hand, reacting to visual cues like a photo or time in role, and tailors the subject line or framing rather than the AI-style personalized first sentence. AI tools all pull from the same databases, she says, so she wants a "back door in" rather than the front door where everyone is trick-or-treating. She keeps her target list in her head, and when the founder asks where to start she says to look at who is "in flow" with you and who the next adjacent ring of early adopters is.

Justin's last point is that when a prospect says they already have a solution, Abel does not argue. She agrees that the tool is good for that, then pivots to taking them further upstream with value. This is what selling to the alpha looks like in practice.

Her closing advice is that sales is about learning fast from rejection, and that founders should not be afraid to send many notes to people they can deliver real value to, or to ask hard questions. People want access to something that feels different, yet most companies commoditize themselves by mimicking what everyone else does, such as simply copying the forward-deployed engineer label. Her summary: "don't be better, be different."