Insights & News
Resources for technical Founders
Best practices on Founder-led company building, how to scale your business, attract world-class talent, and challenge conventional approaches on what it takes to win in today's market.
Hiring the Right Account Executive
As Series A and B rounds get harder to raise, founders look for shortcuts to their next revenue milestone. Why your first sales hire usually shouldn't be the $500K whale hunter — and the questions to ask before you interview anyone.
Mutual Action Plans Are Awkward
The sales tactic that makes founders cringe — until it's done right. How to turn a Mutual Action Plan into a collaborative tool that de-risks your pipeline and keeps deals on the rails.
The Founder-Led GTM Starter Pack
The hard requirements for founders of early-stage technical companies. Consider this the 'Rippling stack' for early-stage GTM — the tools that let your founding team be data-driven at a fraction of the legacy cost.
So What Does It Cost?
In a tough market, prospects ask about price on the first call. But the question is rarely about price — it's about whether they can scale. Seven questions founders should ask before answering.
Like It or Not, the Big Keynotes Tell You What Prospects Want
Keynotes and mainstage sessions tell you exactly what your prospects want to hear. Learn how to mine that language and outmaneuver the market shapers on the ground.
The Pain of Asking for Pain
Awkward discovery questions like "What are your challenges?" rarely work. Here's how founders can earn the right to uncover real pain and build the first version of their sales playbook.
What Does My Team Think?
Meeting the CTO who can sign isn't the same as winning the deal. Learn how to use executive relationships as peers to navigate into the team that actually evaluates and implements your product.
You Can Never Truly Offload Prospecting
Founders rush to hand off prospecting as "low leverage" work. Here's the checklist of what you must own first—and a two-hour plan to start building pipeline yourself.
You Need to Show Something on the First Call
Prospects have too many options to sit through 30 minutes of discovery without seeing your product. Here's a minute-by-minute framework for demoing on the first call the right way.
There's a Lot of Ways to Fit, But Don't Confuse Revenue with PMF
A solid revenue number is the milestone investors signal as the first sign of Product-Market Fit—but revenue alone isn't PMF. Here's how to tell the difference between a $1M ARR win and a company built to hit $100M+.
Revenue-Generating Products Are Definitive
Avoid being 'everything for everyone' to build a real product. Why repeatability isn't just about bringing in revenue — it's about solving a repeatable problem that brings in revenue and gets you to your first $10M+.
Budget Owner Doesn't Mean Buyer (or Signer)
Teams of every size confuse the Economic Buyer, the Signer, and the Budget Owner. They're distinct roles that only sometimes overlap — and knowing the difference is often what closes your deal this quarter instead of next, or ever.
I Might (Definitely) Need Security
SOC 2 Type II is a good starting point, but it's rarely enough to clear a prospect's security requirements. The internal steps founders can take to keep security from slowing down a deal.
ROI Refresh in Founder-Led Sales
Business cases need to be CFO-ready at almost any dollar amount. The three areas where impact lives — increase revenue, reduce cost, reduce risk — and how to build a defensible case for both incumbents and category creators.
Should a Deal Take This Long?
Founders closing their first $1M+ in revenue keep asking whether deals of a given size should take this long. The honest answer: it depends on how many people must reach consensus. Stakeholder benchmarks from single-user to strategic deals.
You're Probably Not Going to Get a Meeting with the CFO
Before sending any proposal, ask: what happens if this lands on the CFO's desk? Since you likely won't get that meeting, your business case has to win on its own. The qualification, business case, and approval questions to answer first.
Non-Obvious, Obviously Big Markets
Some of the greatest breakout software companies didn't obsess over market size initially. How the best companies identify non-obvious, high-potential markets by talking to the smartest, best-aligned people.
Make It POP: Partnership Onboarding Plans
Prospects fear what your product costs at scale long before the first contract is signed. A Partnership Onboarding Plan scopes what's being evaluated now, what's validated but out of scope, and what's future state.
Shared Learnings Lead to More Earnings
Dashboards are easy to hide behind. A culture of Shared Learnings gets your team comfortable surfacing the good and the bad, making pipeline far more predictable.
Sales Candidate Checklist: Screening
Sellers are great at selling themselves, which makes the first AE hire risky. A screening checklist and the exact questions to ask on your first call.
Product-First Drives More Revenue
For new categories, traditional formal selling isn't what wins customers. Why product and technical outcomes must be the focus to generate future revenue — and who to hire first.
Planning Is the Most Important Step
Mutual Action Plans put structure around the evaluation, but deals still stall. Internal Close Plans hold you and your team accountable — and make selling a team sport.
More on Sales Prospecting as an Engineering Problem
Modern GTM stacks make the tedious parts of outbound obsolete — and only one piece relies on AI. Why technical, process-oriented founders are built for the future of sales.
Sell Your Roadmap
Deliver on your promises and have customers for life. Done right, selling roadmap drives deals faster, sets clear expectations, and delights customers with what they bought today and what's coming next.
Inspire the Next Step and Win More
Founders and sellers too often ask the customer to lead. If you don't inspire and guide your prospect on how to engage, expect vague next steps and lost deals.
Increasing Deal Size Isn't the Only Way
When revenue is growing but burn is mounting, the common advice is 'increase deal size.' But ARR and NRR tell a bigger story — sometimes smaller, faster deals win.
Growth Is Key, But So Is Retention
Everyone loves 'up and to the right,' but most founders lose sight of their most impactful cohort: existing customers. A framework for knowing when you're in retention mode vs. growth mode.
Events Are Your Best Way to Build Pipeline
Looking to build top of funnel? Events. Developers your target persona? Events. How to build pipeline around any conference, on any budget.
Context Is the Unlock
As a company scales past PMF, the CEO's job becomes the manufacturing, distilling, packaging, and dissemination of shared context. Here's what to ground your team on.
Conserve POC Calories
Time is scarce and closing is hard enough. Ask hard qualifying questions upfront so you don't burn effort on a prospect who was never likely to buy.
Bring Clarity to What You Do First
A major failure mode at every stage is the inability to clearly describe the problem you solve. Before ICP, outbound, or ROI, you need a one-sentence articulation of your value.
Avoid Slipped Deals
Every B2B founder has felt the pain of a slipped deal. Before you blame factors outside your control, here's the checklist to make sure you've pulled every lever first.
Are You Prepared for Your Discovery Call?
Teams use AI to prep for calls, but most don't understand why they're gathering research. The key insights you should have before entering any discovery call.
Enterprise-Wide Sales Activities
GTM is a full-contact, team sport operated jointly across every domain. Revisiting Mark Leslie's Sales Learning Curve and why founders own every problem and every solution.
Technical Wins Win Deals
Every deal has two parts: Technical + Business. Without the technical win there is no champion, and without a champion there is no deal. Why founders must master the technical win first.