When to Hire a CRO for Your Startup

Some things that make me cringe / want to throw up when I'm auditing a 𝗽𝗿𝗲-𝗿𝗲𝘃𝗲𝗻𝘂𝗲 (𝗼𝗿 𝗲𝗮𝗿𝗹𝘆 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 < $𝟮𝗺𝗺 𝗔𝗥𝗥) startup's GTM - # 𝗜𝗻𝘃𝗲𝘀𝘁𝗶𝗻𝗴 𝗶𝗻 𝗲𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲-𝗴𝗿𝗮𝗱𝗲 𝘁𝗲𝗰𝗵 Yep - those of you out there paying for Salesforce, Gong, and ZoomInfo to name a few. It's not necessary! Start with the true startup stack (HubSpot, Fireflies/Otter, and Apollo) and 𝘤𝘰𝘯𝘵𝘳𝘰𝘭 𝘺𝘰𝘶𝘳 𝘣𝘶𝘳𝘯. Your pipeline and sales process is not complex enough to warrant that kind of monthly spend. As one of my clients put it - "It's like giving a Ferrari to a baby". #2 𝗛𝗶𝗿𝗶𝗻𝗴 𝗮 𝗳𝘂𝗹𝗹-𝘁𝗶𝗺𝗲 𝗩𝗣 𝗼𝗳 𝗦𝗮𝗹𝗲𝘀 / 𝗖𝗥𝗢 NOPE. 𝗬𝗼𝘂 Mr/Ms Founder are the CRO until you have strong signs of PMF. No one else can do this job but 𝘺𝘰𝘶. Need help? Hire a 𝘧𝘳𝘢𝘤𝘵𝘪𝘰𝘯𝘢𝘭 CRO/VP of Sales. For that maturity, 10-20 hrs a month is all you need from a senior sales resource. You need to be the one driving pipeline, sales to close, and collecting that golden product/user feedback 𝘧𝘪𝘳𝘴𝘵𝘩𝘢𝘯𝘥. #3 𝗛𝗶𝗿𝗶𝗻𝗴 𝗮𝗻 𝗶𝗻-𝗵𝗼𝘂𝘀𝗲 𝗦𝗗𝗥 This is the most junior sales role out there. I repeat - 𝗺𝗼𝘀𝘁 𝗷𝘂𝗻𝗶𝗼𝗿. You (very likely) don't know how to manage or coach them....so you are setting both of you up for failure. Either hire a fractional sales leader to help you hire / train / coach them OR just hire an SDR agency. There are in fact good SDR agencies out there. It's a cheap, low-risk way to test this channel. And bonus - the agencies do this every day for dozens of clients. They are pros that cost the same as the entry-level novice does. #4 𝗜𝗻𝘃𝗲𝘀𝘁𝗶𝗻𝗴 𝗶𝗻 𝗲𝘅𝗽𝗲𝗻𝘀𝗶𝘃𝗲 𝗺𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴 (𝗲𝗴 𝗽𝗮𝗶𝗱 𝗮𝗱𝘀 𝗼𝗿 𝗮 𝗣𝗥 𝗮𝗴𝗲𝗻𝗰𝘆) 𝗕𝗘𝗙𝗢𝗥𝗘 𝘆𝗼𝘂'𝘃𝗲 𝗱𝗼𝗻𝗲 𝘁𝗵𝗲 𝗼𝗿𝗴𝗮𝗻𝗶𝗰 𝘀𝗰𝗿𝗮𝗽𝗽𝘆 𝘀𝘁𝘂𝗳𝗳 When you're this early, you usually don't have a strong website, brand, or positioning. Yet - some of you are burning $10k a month on a fancy PR agency or on paid ads. The PR agency and the ads are just driving traffic straight to your....sorry, but sh*tty website. Likely with poor positioning or CTAs. Also - often, you don't have the tools in place to track* the performance of these channels, nor do you know what 'good' metrics look like. This is a total waste of your cash. Do the scrappy stuff first --> thought leadership via social media, podcast guest appearances, and good ole nurture email marketing. These work, and they cost little to nothing but your time. AND they are more effective in the early days when you're still testing your messaging. There are a few exceptions where something I mentioned above may make sense for you...but it's very rare. ________________________ If you don't know me well, I'm Jess 👋 . Fractional CRO + CMO for B2B startups and coach to fractional GTM executives. Making go-to-market simple(r) and scalable for founders and solopreneurs.

Hiring a CRO too early is a startup kiss of death. "But it's just a title, Amy" is the response I often get. Especially when the founder is interviewing someone they LOVE. Fear kicks in and they don't want to lose the person that sounds like the ticket to that infamous "rocket ship." The problem? It's twofold: 1. There’s a big difference between being a builder, an optimizer, and a maintainer/grower. If you’re an early-stage startup, you need a V1, maaayyyybe V2 builder and optimizer. 2. If you make someone a CRO too early and they're not the person to take you the distance, you'll have to hire "over" them. If they're good and just need guidance, you run a big risk of losing them. Why write a check you can't cash? The responsibilities of a CRO are right in the name: They drive the strategic vision to drive, retain, and grow revenue… across the company.   They are executive leaders of leaders.   A CRO will evaluate and set the strategic direction in each function with a leadership team driving the plan for them. From the layers of Sales, Marketing, and RevOps to Customer Success, Account Management, Integration, and Implementation. Think of CROs like the glue connecting all your customer-facing departments around a shared goal: to drive revenue. If you're asking questions like these: 📍 Do you understand your market and buyer journey? 📍 Are you still figuring out your ICP? 📍 Is your revenue growing? 📍 What does your sales process look like? 📍 Do you know why your customers buy, why they stay, and why they leave? 📍 How repeatable is your process? 📍 Is the product ready, and can it deliver? 📍 How do I build a sales team? 📍 I just hit $1M in ARR; how do I continue to grow? 🛑 STOP 🛑 And hire a Head of or VP of Sales instead. Getting "Windex clear" about what needs to be done at your startup today and in the near term is critical to the health of your business. And then hire for the work that needs to get done now with someone competent to do it. For the record, in the last almost 30 years, I only know TWO people that went from ~10M to $100M ARR+ They started as VPs of Sales while earning promotions along the way to get to CRO. That's it. Get clear first. Then double down on an effective interview process. If you need one, my hotline is on ☎️

A little over 5 years ago, I managed to build a small community of 22 startup founders. Over the years it's grown a bit to 46 company founders who share their stats both good and bad confidentially. One of the latest studies is around one of the most critical hires startups make - the CRO hire and the news is pretty dismal. Across a cohort of 32 Series A/B startups, 60% of newly hired CRO/CCOs left or were fired within 12 months. This level of churn disrupts pipeline, burns cash, and creates board tension and really sets the company back a year or more. WHY? Too early ----------- GTM not repeatable. ICP, ACV, pricing, win reasons, cycle time still moving. Too little volume. 1–2 reps, thin TOFU. A CRO adds leverage once there is a team and 3x cov. Missing scaffolding. No clear qualification, forecast rubric, enablement, comp, or mktg engine. Wrong archetype -------------------- Basketball coach asked to run a Football team. Talented leader. Different sport. Scaler from $50M+ ARR dropped into PMF‑proof stage. Velocity field leader dropped into long enterprise deals. Process‑first operator where narrative selling and bespoke deals win. Expectation mismatch ------------------------- People leader vs player‑coach. Founder needs daily deal work and a carried number. Hero culture vs instrumentation. Company needs pipeline math, stage conversion, weekly inspection. Budget runway gap. Candidate expects headcount and brand spend. Company needs staged hiring tied to payback. Fast mis‑hire signals ---------------------- Light discovery on ICP, payback, stage conversions. Heavy focus on title, span, budget. Refs rave about team leadership, light on specific deals they personally created. Big guarantees. Little variable tied to early milestones. Readiness checklist ----------------------- Hire a CRO only when most are true: 3 consecutive qtrs with stable ICP, ACV, win rate, cycle. 4+ reps with 60–70% at or above quota. Capacity model and playbooks documented. 5+ references in core ICP who speak to outcomes. If several gaps remain, use a VP Sales or Head of Growth as player‑coach to prove repeatability, document the motion, and build the first mgr layer. I empathize - founders are exhausted building product, raising, and selling. Hiring a senior commercial leader can feel like relief. Rushing this hire damages the company, the team, and board trust