Startup Hiring Guide

Something strange is happening in startup compensation right now. Especially in AI. And it’s not in your favor. Companies are raising massive rounds at sky-high valuations. But they’re doing it with far fewer employees than ever before. It’s not uncommon to see a company that has raised $1b at a $20b valuation. And has just 200 employees. A company with that profile just a few years ago would have had well over 1,000 people. Yes, companies have always raised big rounds. But not with this much capital and this little headcount. Why does that matter? Because companies are still using compensation benchmarks from that older world to determine your equity offer today. That is not just outdated. It is fundamentally broken. --------- When a company raises a priced round, they typically refresh the employee option pool. That number is often 10%. That 10% is meant to cover all employee equity grants until the next fundraise. In the past, that pool would have been designed to support 500 to 1,000 hires. Today, many of these companies are hiring only 150 to 300 people. That is a fraction of what the pool was originally designed to support. That 10% is being stretched across far fewer people. Which means each person should be receiving significantly more. But that is not what is happening. Companies are handing out grants that seem reasonable, but they are based on an old standard that no longer fits the structure of the business. If you’re a candidate, this matters. A lot. You are being compared to benchmarks that do not reflect the company you are actually joining. You should be asking for more. More equity. More ownership. More transparency about the hiring plan and pool structure. Just because the market hasn't corrected for this yet doesn't mean you shouldn't.

Founders are often advised to ��hire the best people,” which sounds good in theory but isn’t realistic for most. Here’s why this advice misses the mark: Early on with Chezie, I posted an engineering role with a $120K salary. A Silicon Valley leader straight-up told me, “That’s pretty low; you’ll have trouble recruiting.” And she was right. Most applicants were junior devs, not the “rockstar” hires investors envision. And as I saw other founders making high-profile hires, I noticed a pattern: nearly all of them had raised millions in funding. When investors tell you to “hire the best,” they’re often picturing someone with a resume from Stanford or Google—a “best” that’s incredibly costly and exclusive. This advice overlooks talent from less traditional backgrounds and ignores the financial reality for most founders, especially those who are bootstrapping or underfunded. Here’s what worked for us instead: 1. Redefine “best” - The “best” hire isn’t just someone with a prestigious resume; it’s someone who believes in your mission, fits your budget, and has the skills to grow with you. 2. Hire strategically, not full-time - Before making a full-time hire, exhaust software solutions and part-time contractors. Scale up only when absolutely necessary. 3. Be transparent about compensation—Listing salaries and equity openly filters out mismatches and helps you attract the right candidates who are on board with your mission. My advice to founders? Hire the best YOU CAN AFFORD. Focus on making every hire count without breaking the bank. Want to learn more about building a world-class team on a startup budget? Subscribe to my newsletter, Equity Shift: https://lnkd.in/eJjCSSCe

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 ☎️

I often see many startups conducting  intensely rigorous, FAANG-style technical interviews. In my view, this is frequently counterproductive and a waste of time. If you're an early stage startup, you don't need to hire experts who can build massive scale systems like Google or Meta right out the gate. What you need are smart, adaptable team players who can get an MVP launched. My advice is to focus on hiring for general programming competency, business domain knowledge, and cultural fit. Look for people who can develop APIs, configure cloud services, and write just enough code to get your product off the ground. Even if you aim to someday scale to millions of users, today's abundant managed services enable that without reinventing the wheel. The priority should be launching a solid v1. Implementing convoluted algorithm tests and system design exercises often deters great candidates for no good reason. Of course, technical rigor matters at some point. But initially, prioritize hiring product-focused builders who understand the business challenges and can evolve with the company. Ultra-complex interviews are overkill for most early stage needs. While tempting to emulate big tech, that bar often doesn't make sense. Focus on the skills that will propel your core product forward and avoid deterring strong startup contributors unnecessarily.

Hiring never seems to get easier as a founder. I’ve managed to fuck it up left, right, and sideways. So I took each of these fuckups and turned them into a list of questions I must answer before giving an offer. I call it my “Don’t fuck this up again you silly little man” checklist. 1) Is the job crystal clear (in terms of the 3-5 core responsibilities)? 2) Are the skills crystal clear (in terms of the 3-5 qualifications needed to do the job well)? 3) Are the deficiencies of the candidate clear? 4) Are the deficiencies a dealbreaker or is there a clear path to mitigate them? 5) Has this candidate been compared against another high quality candidate (such that the decision isn’t driven by feeling rushed or by emotion)? 6) Has this candidate demonstrated substance and not just salesmanship? 7) Does their comp make sense financially for the business? 8) If you have to fire this person in 6 months, what would the reason be? 9) How can you avoid that scenario happening?

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.

"We need to hire fast!" is hurting your startup. I work with founders and hiring leaders scaling their teams. I keep seeing the same pattern: The pressure to fill a role quickly leading to surface-level hiring. → A few quick interviews. → A gut decision. → A rushed offer. Speed matters. But speed without strategy is expensive. And here’s what happens next: → 6-12 months of wasted runway You hire someone who looks great on paper but doesn’t deliver. → Team morale declines Your best people pick up the slack—until they burn out or leave. → Market momentum slows Mis-hires don’t drive results, and now you're playing catch-up. → Customer trust fades Inconsistent execution leads to missed deadlines and dropped deals. Then reality hits: You spend 3X more time and money fixing the mistake than you would have spent hiring the right way. Here’s what to do instead: 1. Define the win before opening the role.      What must this hire achieve in 6 months?      If you can’t answer that, you’re not ready to hire. 2. Cut through the fluff.      Structured interviews > generic Q&A. 3. Assess real-world ability.      Forget the “culture fit” trap.      Can they actually do the work at the level you need? 4. Get buy-in early.      Alignment upfront means fewer roadblocks later. 5. Move fast—but never reactively.      Hiring with urgency is smart.      Hiring out of panic is expensive.      Hiring with a STRATEGY makes the magic happen. When the right person is in the right seat, everything moves faster and smoother. Your business THRIVES. What strategy do you implement to hire quickly the right way?

Startups keep making the same hiring mistake. They recruit in waves—hiring when they need someone, then stopping until it’s an emergency. Suddenly, they need a key hire yesterday and scramble to find the perfect person in a tiny, competitive talent pool. This approach doesn’t work. If you want to attract top talent, recruiting has to be a constant priority. Here’s how: 1️⃣ Build relationships before you need them Make connections now, not when you’re desperate. Send messages, ask for intros, and check in with people regularly. Play the long game. The moment a great candidate is open, you should already be top of mind. 2️⃣ Create a culture people rave about Your best hires will come from your team’s network. If your employees love where they work, they’ll bring their best people with them. Make it easy for them to refer others by building a culture worth talking about. 3️⃣ Refine your pitch Why should someone choose you over the 10 other opportunities they have? Your messaging needs to be clear, compelling, and aligned with what your ideal candidate actually wants. If it’s not landing, tweak it until it does. 4️⃣ Be loud about your wins People want to join teams that are going places. Share your milestones, showcase your team’s work, and let people see the momentum. The best candidates aren’t just job hunting—they’re looking for the right story to join. Great companies are always recruiting. If you’re waiting until you need someone, you’re already behind.

We need someone with 10 years of experience. Really? Let me challenge that thinking. The most successful hires I've seen aren't always the most experienced - they're the ones with the highest potential. Here are 8 uncommon traits that signal high potential in candidates (backed by research): 1. Aspiration & Self-Leadership - Takes initiative without constant direction - Aligns personal goals with company objectives 2. Learning Agility - Adapts quickly to new situations - Applies new skills effectively 3. Emotional Intelligence - Shows high self-awareness - Demonstrates genuine empathy 4. Strategic Thinking - Makes informed decisions - Thinks beyond current role 5. Growth Mindset - Seeks learning opportunities - Views feedback as development 6. Cultural Alignment - Builds trust naturally - Contributes to positive workplace dynamics 7. Resilience - Thrives in uncertainty - Maintains performance under pressure 8. Self-Motivation - Consistently delivers results - Goes beyond job requirements While technical skills can be taught, these character traits and potential indicators are much harder to develop. The next time you're hiring, look beyond the years of experience.  Focus on these traits instead. Your future top performers might not have the perfect resume - but they'll have these qualities in spades. Agree?  Disagree?  Share your thoughts below. 👇

Over the past decade, I've hired 500+ people and interviewed thousands. Here are 6 traits I’ve found to be the best predictors of a great hire: ~~ 1) Speed of Response The faster someone responds, the better they’ll likely fit with me and my team. It’s not about having all the answers right away—it’s about engagement, care, and showing you’re present. That level of responsiveness is invaluable. == 2) They Demand Excellence Great hires hold themselves to a high standard and expect the same of others. When something goes wrong, they own it. Their first instinct is to ask: ➝ What can we learn? ➝ What needs to improve? This attitude turns problems into progress. == 3) Humility The best team members are hungry to grow and leave their ego at the door. They don’t pretend to know it all; they ask questions, seek feedback, and adapt. Over time, these learners become irreplaceable assets to any team. == 4) Proactive Problem Solvers They don’t wait for instructions—they take initiative. When they see an issue, they address it. When they encounter a roadblock, they suggest solutions. Proactive hires reduce bottlenecks and keep the team moving forward. == 5) Strong Communication Skills Clear communication is critical for collaboration, especially in remote and fast-paced environments. The best hires: ➝ Ask thoughtful questions. ➝ Share updates without being asked. ➝ Document decisions to keep everyone aligned. == 6) Alignment with Values Skills can be taught, but values are harder to change. Does the candidate embody the core principles of your team or company? Those who align with your mission are far more likely to thrive and contribute over the long term. == Hiring isn’t just about filling a role; it’s about building a team of people who can challenge, inspire, and grow together. What traits do YOU prioritize when hiring? Let me know. ⬇️