Key Takeaways: Sales Masterclass and Founder Office Hour with Ryan O'Holleran (Anthropic, Stripe, Airwallex)
Last week, we had the privilege of hosting Ryan O'Holleran for an Elsa Capital founder office hour and sales masterclass. Ryan is Anthropic’s Head of Sales, Enterprise & Startups - EMEA, and formerly led Enterprise Sales at Airwallex and was the #1 global sales rep at Stripe.
Given the overwhelming positive response to this session, we're planning another founder office hour with Ryan in July, and with other operators and experts in future. If you’d like to join our future office hours to learn from the best in class operators, sign up here and we will notify you of our future events. We look forward to supporting you on the founder journey!
In addition, we want to thank the Anthropic team for providing API credits and access to higher rate limits through the Elsa Capital x Anthropic Startup Program.
Below we are sharing some key takeaways from this session.
ATL vs BTL: Know Your Altitude
One of the most critical frameworks: "Is this an ATL or BTL buyer?"
ATL (Above The Line) buyers are often C-level executives, heads of innovation/AI focused on increasing revenue and decreasing costs
BTL (Below The Line) buyers are often direct users, i.e. operators dealing with tactical problems
Make sure you give the right messaging (ATL vs. BTL) to the right stakeholders in the sales process.
The key trap: salespeople often nail the BTL value proposition, then when they get access to ATL executives, they deliver the same BTL presentation. The deal loses energy and momentum dies.
The AI-Native Sales Reality – what traditional B2B SaaS sales wisdom are now outdated?
We're in a unique moment where "buyers are learning how to buy, sellers are learning how to sell—everyone is trying to get educated at the same time."
Ryan talks about a few specific areas where traditional B2B SaaS sales wisdom may be outdated when selling AI-native products.
Feature-first demos are outdated → Show outcomes and ROI from AI insights instead
Controlling the data narrative is outdated → Address AI trust and data privacy concerns upfront
Annual contracts as standard is outdated → Consider usage-based pricing and shorter proof-of-value periods
The Golden Rule of ICP: Bad Customers Are 10x Worse Than No Customers for Early Startups
"Signing a bad customer is 10x worse than not signing them," Ryan said. This isn't just about support headaches—bad customers drain engineering resources, create negative case studies, and prevent you from learning what drives real value.
The key is understanding not just who your customer is, but how they buy. Ryan breaks buyers into three personas:
Songbird: Agreeable, says "that's great" to everything
Owl: Analytical, asks endless who/what/where questions
Rhino: Direct, results-focused
Your entire sales approach must adapt to their buying style.
Hiring: Leverage Networks + What to Look For in Your First GTM Hire
For early stage startups, 90% of successful sales hiring happens through networks and referrals.
In addition, don't just hire traditional sales backgrounds. At Stripe, some of the best sales performers were founders, MBAs, ex-consultants, etc. Hire people who can think strategically.
For early-stage startups, the profile for your first GTM hire should prioritize:
Ideal profile: Startup experience, comfortable with ambiguity, builder mentality
Red flags: Only worked with mature processes, needs extensive support systems
Interview focus: Problem-solving ability, grit, and coachability over pure experience
Compensation structure: Base + commission with accelerators for overachievement
Now is the Land Grab Time
"Now is land grab time." Don't let annual contracts prevent customers from trying your product. Give them 2-month trials. Get market share now—contract optimization comes later.
The outdated approach of forcing annual commitments upfront can cost founders deals in this fast-moving market with AI products.
The Power of Trumpeting
Use your investors strategically for ATL touchpoints. Multi-thread early in the sales process.
Make noise at the C-level early. The C-level executive who signs off on the budget shouldn't hear from you for the first time when you're trying to close a deal.
Become an Extension of Your Customer
Become the path of least resistance for your customers in the sales process. Ask yourself: "What can I do to help them?" Sometimes that means putting together the ROI analysis for them.
Building Credibility the Effective Way
Events and booths are often dead money (especially for budget-conscious startups). Better approaches:
Sponsor coffee carts at conferences—everyone's holding a cup with your logo
Speaking engagements beat booths every time
Social proof is extremely important—obsess over getting the right logos early
Given the overwhelming positive response to this session, we're planning another founder office hour with Ryan in July (and with other operators in future). If you’d like to join our future office hours to learn from the best in class operators, sign up here and we will notify our next events. We look forward to supporting you on the founder journey!
Big thank you to Ryan for sharing his 10+ years of hard-earned sales wisdom with our founder community.