Jan 16, 2023 · 29m · product-market-fit
Adrian Camara, Founder of Athennian | How to do Customer Discovery · PMF Show
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Adrian Camara, founder and CEO of Athennian, shares his journey of building a $50M entity management platform by conducting deep paralegal customer discovery, navigating co-development crises, and scaling via a mid-market B2B SaaS strategy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Pablo holds 19.5% of the talking time here. How this is scored →
Pablo as informed peer 4.4 Guest teaching 5.4 Guest disagreement 0.6 Pablo pushing back 0.4
speaking balance: gold is Pablo, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:51 Refusing client product demands
Adrian forcefully explains why they walked away from demanding customers who wanted custom features without matching financial stakes.
Hardest push from Pablo ▶ 13:36 Pushing on customer-as-PM riskPablo challenges the co-development approach by arguing that it risks turning non-technical clients into micromanaging product managers.
Biggest teaching moment ▶ 20:15 The software requirements icebergAdrian educates first-time founders on the reality that stated enterprise requirements only represent 30% of what is actually needed to get paid.
Pablo holds their own ▶ 19:34 Enterprise budget reality checkPablo demonstrates domain knowledge regarding enterprise spending habits, noting that hesitation on a 10k deposit is a red flag on problem severity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Pablo as informed peer | Guest teaching | Guest disagreement | Pablo pushing back | Why |
|---|---|---|---|---|---|---|
| Defining the Mid-Market B2B SaaS Sweet Spot | 5 | 4 | 0 | 0 | Pablo sets the premise around the mid-market SaaS sweet spot versus enterprise and SMB. Adrian elaborates on his background as a corporate lawyer discovering data management inefficiencies across complex entity structures. | |
| Identifying Who Suffers from Entity Management Problems | 3 | 6 | 1 | 1 | Pablo asks whether the problem lies with law firms or corporate clients. Adrian explains that it affects everyone across legal, tax, and finance, sharing an illustrative due diligence experience involving 500 physical binders. | |
| Deep Screen-by-Screen Legacy Software Teardowns | 4 | 6 | 1 | 0 | Pablo asks how focus groups were structured. Adrian details their methodical discovery process, including having law firms assign matter numbers for paralegals to deconstruct legacy software screen by screen. | |
| Establishing Early Credibility Using Discovery Insights | 5 | 5 | 0 | 0 | Pablo notes the wisdom in extensive discovery rather than rushing into code. Adrian contrasts this with competitors who built from an attorney's perspective and explains how his teardown diagrams became his primary early sales pitch. | |
| Managing Co-Development Risks and Firing Misaligned Clients | 5 | 5 | 1 | 1 | Pablo highlights the risk of co-development turning customers into product managers. Adrian agrees and details having to fire two unaligned clients who demanded custom features without financial commitments. | |
| Early Fundraising and Overcoming Major Customer Setbacks | 6 | 6 | 1 | 1 | Pablo and Adrian analyze pricing psychology and founder leverage, comparing large enterprise budgets against required upfront commitments and the unseen 'iceberg' of enterprise software requirements. | |
| Pivoting Go-to-Market Strategy to Mid-Market | 4 | 6 | 1 | 0 | Adrian explains why Athennian pivoted from lengthy 18-to-36-month enterprise sales cycles to the US mid-market, noting the distinct volume game and geographic advantages. | |
| Leveraging Hub-and-Spoke Law Firm Referrals to Scale | 3 | 5 | 0 | 0 | Pablo asks about early mid-market acquisition. Adrian breaks down the hub-and-spoke dynamics of law firms naturally referring corporate clients, driving Athensian's initial million in ARR. |
Statements from this episode (14)
Srugo: Mid-market SaaS is a sweet spot between enterprise and SMB
“Like people oftentimes don't like selling enterprise because it's too slow. It's too chunky. And SMBs oftentimes don't really have the sort of, you know, structure and size and capital to be meaningful customers. So this mid-market tends to be a sweet spot for…”
Camara: Entity management market is 50/50 spreadsheets and legacy software
“The market's like, 50, 50 brownfield and spreadsheets where, you know, brownfield is legacy, really old legacy stuff that you have to rip and replace, you know, out of the market.”
Camara: Founders should extract the wisdom embedded in legacy software
“There's a lot of wisdom built in legacy systems. People dismiss them as old and clunky at the time they weren't. And at the time someone went through a product process. Over years and years and years to build something. And there's tons of wisdom in those lega…”
Camara: Competitors struggle by designing for lawyers instead of paralegals
“We have some competitors today and had a very similar origin story to me where corporate lawyers observed the problem. They missed that step of like, okay, we got to sit down and spend six months with the primary users of this product. And tear down their day …”
Camara: Athennian used customer discovery workflow charts as its year-one sales pitch
“Showing those early customers, the work we put in, like that was my sales pitch. I literally brought up those Visio charts was just like, you know, like kind of like a mirror board type of thing. And like, that was my sales pitch for the first year is I sat do…”
Camara: Delivery-contingent enterprise contracts create massive startup risk
“Our first, like our first iteration of our first customers, they were contracts with deposits, but the balance was due on delivery of the product, which is when you're selling into, you know, mid market enterprise, that's super high risk because the definition…”
Camara: Enterprise co-development requires champions willing to take career risk
“The one thing that I realized is like, if you want to do this co-development process with mid-market or enterprise, you have to find people in those organizations that are willing to take a lot of risk.”
Camara: Athennian lost its anchor co-development partner 30 days after raising $500k
“I raised that on the strength of a large logo co-development partner. Who then the relationship literally dissolved 30 days after we had closed that half a million dollars.”
Camara: Founders should not write code without six-figure deposit commitments
“My threshold, if I ever do this again, would be I would not start cutting a line of code unless I can get, you know, six figure order form deposits on the basis of a PowerPoint deck. If I'm unable to do that, I either have not identified a painful enough of a …”
Camara: Stated enterprise software requirements represent at most 30% of build needs
“What they tell you is probably, you know, 30% at most of what you need to actually build to get that cash flowing. And that said that 60 to 70% is that unspoken requirement of, you know, assumptions.”
Adrian Camara: Realistic enterprise SaaS sales cycles run 18 to 36 months
“If you're being realistic about enterprise, like look at the benchmarks, it says 12 to 18 months. That's the best case scenario, right? Like it's really three years, depending where it's like, you know, 18 months to three years.”
Camara: Canada lacks a strong mid-market compared to the US
“Canada doesn't have a very big mid market, but the United States does. And I, you know, and I think that's one thing that, that, that does create some inefficiency in Canadian founders is in their home market. There's not a great mid market.”
Camara: Athennian refuses contract addendums unless features are pre-planned on roadmap
“We very, very, very rarely make product commitments on contracts and stuff like that, unless it's something, it's already on the roadmap, and maybe we're bringing it forward by six months, we were going to do it. In Q four, we'll do it in Q two, if that's what…”