Jen Abel

Starting with a deep understanding of a market problem accelerates the path to PMF, whereas starting with a technical insight is riskier but potentially has higher upside.

"I think product market fit when you start with the market first, it's accelerated. ... Starting with a product is a hell of a lot riskier."

Aggressive discounting is a sign of poor qualification; high-value clients who are truly bought in will respect the price.

"In the very early days, people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you. If they're sitting there ni..."

Startups should aim for an initial enterprise ACV of $75K-$150K to align with corporate buying habits and avoid anchoring at a low price.

"Enterprise companies are very used to a land, when I say the first initial contract, somewhat between 75K and 150K, very used to that. In fact, that's probably where you want to start because you also..."

Effective enterprise positioning focuses on 'gap selling'—the distance between the current state and a future opportunity—rather than just solving technical problems.

"You need to vision cast, you need to sell to a gap, don't sell to a problem. There's a very big difference between problem selling and gap selling. Problem selling is highly specific, more technical t..."

Winning in the enterprise requires radical differentiation to avoid being commoditized in a three-way vendor comparison.

"As soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. Here's what you will be able to do tomorro..."

Vulnerability and honesty about being early-stage encourages prospects to provide raw, honest feedback rather than polite platitudes.

"I would be very open and honest with where you are. Hey, I'm an early stage startup. We have a lot to learn. Can we kind of gain your insight into how this problem is manifesting on your side?"

Founders must filter user feedback from design partners, distinguishing between requests based on 'the old way' and insights that reveal true market needs.

"It is the founder's job to interpret that because a lot of feedback you get is this is the old way, they're responding this way because it's the old way of working... 80% noise, 20% had I not asked th..."

In the early stages, the founder's novel insight and subject matter expertise are the primary drivers of interest before a brand or product is fully established.

"Founder led sales is really that first milestone that a startup goes through on the commercial side, which is, how do I go out and get my first few customers? ... the founder is the product."

Effective cold outreach relies on immediate relevancy and a counterintuitive hook rather than generic personalization.

"If you can focus the messaging in a way that speaks to something that has a bit of shock value, or is counterintuitive, you'll get them to continue reading. ... relevancy. I think that matters even mo..."

Manual lead generation and outreach are necessary to identify the correct parameters and messaging before attempting to scale with automation tools.

"Before you buy any tool, don't even think about tools. ... Can you manually find 30 people that you want to spend 15 to 20 minutes writing a rock solid note to?"

The primary goal of early founder-led sales is market research and learning, not immediate revenue generation.

"Founder led sales is not about revenue on day one. It is about learning as fast as humanly possible to get to that pulse, so that you can earn the right to sell."

Maintaining momentum requires securing the next meeting while still on the current call.

"Get the second call booked on the first call. Pull up calendars. Look at calendars. Who else should be invited?"

Most sales failures are actually failures of qualification at the top of the funnel rather than closing issues at the bottom.

"It's qualification. Qualification because if you spend your time on the wrong leads, that equates to a zero. ... it's never a bottom of funnel problem. It's always qualification."

Manual, highly personalized outreach is more effective for high-value enterprise deals than automated AI-driven tools that use the same saturated databases.

"I don't use a tool. The thing about AI tools is they're all pulling from the same databases. I want to email someone not in the database that's getting hit by a million folks. I want to take a back do..."

Hiring sales talent too early can be detrimental because the seed stage requires the founder's ability to experiment and learn directly from the market.

"I have this theory that maybe you shouldn't hire any salespeople until series A, right? Because seed is all about experimentation and proving out that experiment, and then obviously series A is about..."

The best early sales hires are those who can 'cosplay the founder' by selling vision and creatively structuring deals rather than just following a playbook.

"I always say you need people that can cosplay a founder, which is selling the vision, getting them excited, running through a wall to get the deal done and getting creative on ... None of my deals loo..."

Standard enterprise sales compensation is a 50/50 split between base salary and on-target earnings (OTE), with commissions around 10%.

"It's usually 50/50. So it's 50% OTE. So it's 50% base salary, 50% OTE... In technology, it could be anywhere between eight and 12%. So rounds out around 10%."

Procurement is a professional buying function that requires the seller to handle the administrative burden to avoid being sidelined.

"When you get to procurement, you're going to have to do all the work. Make their job easy. ... Give me the forms that you need to fill out. I'll fill them out for you, and you can do it yourself."

Identifying the final signatory (CFO, Legal, etc.) early is critical to prevent deals from stalling at the very last step.

"Know who the signature is, because if they don't know what they're looking at, they're going to kick it out and you're going to lose your queue spot."

The 'mid-market' is a dangerous middle ground; companies should instead commit to either the SMB or Enterprise sales model to avoid hiring and strategy mismatches.

"I say the mid-market doesn't exist because what is a mid-market hire? It's either low end enterprise or upper end SMB, and if you bleed those two games you're going to lose. They're so distinctly diff..."

Tier 1 market leaders are often better early adopters than smaller companies because they are highly motivated to maintain their lead through innovation.

"Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the ... Staying in the number one spot is the hardest..."

Enterprise sales is a creative process of relationship building and custom deal structuring rather than a rigid, repeatable science.

"It's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you."

Selling services is often the easiest way to enter an enterprise because it fits their existing procurement habits and builds trust for future software adoption.

"If they have a very immature way of understanding the problem or they've never purchased technology to solve it to some extent... selling them as service, even though the technology is powering it on..."

Relying on large consultancies (e.g., Accenture, Deloitte) as channel partners is often ineffective because they lack the founder's visionary selling ability.

"The problem with channel partnerships and why I don't believe in them is there are a hundred of you on this list and you're expecting them to sell it on your behalf. Biggest no-no, they're not vision..."

The guest explicitly states that most sales problems are actually qualification problems and provides a specific framework for determining if a lead is worth pursuing.

"It's qualification. Qualification because if you spend your time on the wrong leads, that equates to a zero."

The guest emphasizes 'qualification' as a core discipline—specifically the ability to aggressively filter out bad leads and value 'No' as a successful outcome to save time.

"I am a qualification crazy person. I will not get in on another call with someone because on the first call it's either a yes or a no, there's no in between."