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Mailbag: How Do I Explain a Bad Startup Move Without Killing My Next Interview
Good reps land in bad startups. Own it, show what you learned, refocus on your track record, and keep the resume entry tight. Use clear language that signals maturity, better decision making, and intent to stick and scale.
Jay Green
Nov 52 min read


Why 95% of AEs Never Make It Into Elite Startups…And How To Get There
Most AEs miss elite startups not for lack of talent, but misalignment with what top teams value. Get past the first filter by fixing the gaps: real SaaS experience, proof of overperformance, context on your motion, and a profile that shows durability, relevance, and impact. Use targeted career moves to build the track record elite founders actually buy.
Jay Green
Nov 54 min read


Stop Letting OTE Blind You
Big base + flashy OTE looks great until the math collapses. OTE is built on assumptions about win rates, ramp, pipeline, and market pull. If the product is weak, the territory is sliced thin, or leadership is lost, you won’t see that money. Choose environments where you can win and compound your value.
Jay Green
Nov 52 min read


Pick a Lane and Say It With Confidence
Telling a hiring manager you are open to AE or CSM sounds flexible...but it reads as unsure. Pick the role where you win, back it with proof, and state it clearly. Use simple lenses to choose your lane, then position your story with crisp scripts for AE or CSM so you come across as focused and hire ready.
Jay Green
Nov 52 min read


One Sharp AE Story for Early-Stage Interviews
Interviewing for a new business AE role at an early-stage startup. Bring one sharp story that proves you can create pipeline and close without brand or machine. Frame it like a founder pitch: clear, scrappy, specific. Use scene, hunt, process, product reality, results, and adaptability.
Jay Green
Nov 52 min read


Why Retention Matters (Especially at Seed & Series A)
Losing a top rep at Seed or Series A costs more than pipeline. You lose context, feedback loops, and momentum. Use clear expectations, inclusion in decisions, autonomy, stable comp, visible growth paths, and two-way feedback to keep your best sellers.
Jay Green
Sep 113 min read


The 30/30/30 Rule for Player-Coaches
How to balance pipeline, people, and process as a first-time sales leader. Early-stage startups love the idea of a player coach. The 30/30/30 Rule helps first-time sales leaders allocate time across IC pipeline, coaching and rep support, and process and strategy, with a 10 percent buffer for sanity.
Jay Green
Sep 112 min read


Coaching to Confidence, Not Quota (at First)
Early teams often push quota before clarity. Coach for confidence first. Use clarity-first goals, constant and safe feedback, and small wins to help reps ramp faster. Includes check-in questions and weekly goal templates you can use immediately.
Jay Green
Sep 102 min read


From Founder-Led to Repeatable Revenue
Translating founder magic into a repeatable sales motion is where many startups stall. This guide breaks down why founder-led selling works, why early hires struggle to replicate it, and simple steps to extract your pitch, add just enough process, and make learning a team sport.
Jay Green
Sep 103 min read


Preboarding That Builds Trust (That Doesn’t Require an HR Team to execute)
Simple preboarding reinforces excitement and trust without an HR team. Use five low-lift moves (Week 1 email, resource folder, welcome Loom, lightweight chat, LinkedIn hellos) to build connections and set new hires up to succeed before Day 1.
Jay Green
Sep 102 min read


Your New Hire Playbook: From Offer to Ramp
How to make your next sales or GTM hire feel prepared, supported, and ready to win… even without a formal onboarding program.
Jay Green
Sep 103 min read


How to Close a Candidate Who’s Talking to 3 Other Startups
Here’s how to win top sales talent in a competitive market…without begging or over-promising. Great AEs, SDRs, and CSMs move fast and have leverage. When they’re weighing multiple early-stage offers, it’s not just about comp. It’s about signal, clarity, mission, and momentum.
Jay Green
Sep 103 min read


Run Roleplays with Account Executive Candidates That Reveal Startup-Ready Talent
Most startups don’t need polish, they need proof. Use roleplays that have candidates sell what they already sell. You’ll see how they think, communicate, adapt, and stay coachable in a real buyer scenario.
Jay Green
Sep 103 min read


The Sales Interview Scorecard (That Actually Predicts Performance)
What to look for when you can’t afford to miss. Use a structured scorecard focused on traits like deal ownership, coachability, and sales judgment. Learn what to assess for AEs, SDRs, and CSMs so you can hire with clarity and confidence.
Jay Green
Sep 103 min read


Why Your SaaS Startup Isn't Hiring Sales Reps Fast Enough (It's Not What You Think)
Slow hiring isn’t a scheduling problem. It’s fit. Many teams chase an "ideal" profile that doesn’t want the job. Top reps pick startups with momentum, a product that sells, and some inbound demand, plus comp clarity and career growth. Use the 50% rule, sharpen your offer (bridge pay, simple plan, clear path), and widen the pool with hidden gems, cross-industry moves, and role-based promotions.
Jake Citrano
Sep 108 min read


The First 3 Sales Hires: Roles, Risks, and Red Flags
Your first three sales hires set the tone for revenue, learning, and culture. Get them right and you gain momentum. Get them wrong and you burn time, deals, and trust. This guide breaks down the roles, what to look for, the common risks, and how to avoid red flags so you build a motion that scales.
Jay Green
Sep 33 min read


You Don't Need a CRO (Yet): GTM Roles to Hire Instead
Most early stage startups do not need a CRO. They need revenue. Hiring big leadership titles before your motion is baked creates risk and stalls learning. This piece shows why CRO hires miss early and which roles to hire instead based on stage, with clear scopes, what to look for, and how to talk about the opportunity so top talent leans in.
Jay Green
Sep 33 min read


Pitching Your Startup to Candidates: What Founders Get Wrong
Pitch your startup to candidates like you pitch investors. Many founders undersell when hiring their first GTM hires. This guide shows the common mistakes, what a great pitch includes, and how to tailor your message for AEs, player coaches, SDRs, and CSMs so top talent sees upside, ownership, and momentum.
Jay Green
Sep 33 min read


Job Description: Founding Account Executive
Founding AE job description template designed for early stage SaaS startups. Use this copy ready JD with role pitch, responsibilities, 90 day success metrics, requirements, and why join us. Clean, scannable formatting that reads like great outbound and attracts builders who can sell and help you shape the motion.
Jay Green
Sep 24 min read


Build the Right AE: A Startup’s Guide to Crafting Your Ideal Sales Hire
AE hiring profile for startups. Align your Account Executive profile to your motion and stage so you attract the right candidates and improve retention. Map deal size, velocity, ICP complexity, and pipeline volume, then choose the best-fit AE for SMB, Mid Market, or Enterprise. Includes stage-based guidance and office strategy tips.
Jay Green
Sep 23 min read
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