How to hire the best CRO for your SaaS business — CEO perspective

An old sales joke goes like this: A retiring football (or soccer, for my American friends) coach meets with his younger successor and offers some advice. He hands over three envelopes and tells the new coach to open them in order if the team faces a losing streak.

After some time, despite the new coach’s efforts, the team’s performance declined. Remembering the advice, the new coach opens the first envelope, which reads, “Blame me.” This advice buys time as the coach adjusts tactics and communicates with the team and management.

However, a few months later, the team’s performance dips again. So, the coach turns to the second envelope, which advises, “Blame the team.” This strategy provides another temporary solution as the coach reshuffles the team and brings in new players.

But, as luck would have it, the team’s struggles persist. Reluctantly, the coach opens the third envelope, which ominously states, “Prepare 3 envelopes.”

I’ve encountered several Sales and Marketing leaders in my career who have found themselves in situations similar to the “three envelopes” joke. As a CEO, avoiding hiring mistakes is paramount to prevent financial loss, team demotivation, and lost momentum. This is especially crucial when selecting a Chief Revenue Officer (CRO) or VP of Sales.

To make a successful CRO hire, consider the following criteria based on my personal experience:

1. Timing is crucial when hiring your first-ever VP of Sales, especially in the Startup world. Typically, the first (or even second) VP of Sales hired tends to be a mis-hire and doesn’t stay longer than 12 months. This phenomenon is particularly true for first-time CEOs, who may lack clarity on the right job criteria and have misaligned expectations.

In many cases, when the expectations of the CEO clash with the realities of the early-stage startup environment, they start looking for a CRO replacement. It’s essential to recognize that hiring a VP of Sales won’t magically solve issues like a lack of organic demand for your product or poor product performance. Therefore, it’s crucial to be cautious about the timing of hiring a new VP of Sales and ensure that your team is aligned on expectations for a newcomer.

Avoid hiring a VP of Sales until your startup is ready to scale and build or fund a new sales team. Making the decision prematurely can lead to costly mis-hires and setbacks in your company’s growth journey.

2. Requirements and Sales skills. Build your plan and expectations on the ideal CRO profile. Start from education (any particular grad school?) and work experience. Ideal candidates should have relevant industry, vertical, company company-size success stories. Get some good example profiles ready or (even better) a colleague (industry friend) close to your ideal CRO candidate requirements. Remember that a long corporate career might be a bad fit for a fast-paced Startup environment.

3. Job Description. Since you understand search criteria well, it’s time to create a job description. There are many great examples online, but there are a few critical sections to make it “yours”.

• Company details. Please make sure you put any specifics on company culture and values. Having a fit with company values is critical for every solid candidate. Don’t be shy and ask your candidate to write live examples of your company values situations demonstrated over his/her career.
• Responsibilities. Be as detailed as possible here, list your duties list and clearly explain the “independence” level you expect your CRO to have. That’s the area where most of the discussions with candidates will happen. Be upfront.
• Experience. Don’t just copy/paste here, like “MBA preferred, 15 years of Sales Leadership experience”. All candidates (and Search Agencies) start with an experience fit, so be realistic.

4. Shall you use a Search Agency? It’s a personal preference and depends on your trust in your Recruiting team’s ability to fill the strategic role (do they have the right experience?). My take is that for C-level roles; you should use an agency with relevant experience & vertical expertise. Yes, it will cost you more (usually 20–30% of the base salary), but it will save you valuable search time, and you will have several qualified candidates within a few weeks.

5. What to pay attention to during the interview process. All of us have our unique interview habits and favorite questions. So, I am not going to put a questions list here; just want to highlight some critical topics to address throughout the process

• Be upfront and describe your decision-making process. For example: it will take 5 interviews (and name the team involved) and a maximum of 4–6 weeks for you to decide if there is a perfect fit. I have met many hiring managers proud of their 10+ interviews and 2+ months long interview process. Any sane candidate will just walk away from it, and you will do both of you a favor — saving valuable time.
• Absolutely, requesting a 30–60–180-day plan from your top candidate can be a valuable part of the interview process. You can ask for a signed NDA and share relevant company data. Don’t expect a perfect plan, and it’s impossible to make one after 4–5 calls. But you will be able to see candidates’ approach to the task, and get personal perspective and details level. That will give you some insurance that you both are thinking in the same direction, and your new hire will bring a fresh look and expertise to known problems.
• Superpowers. Ask and identify your top candidate’s “superpowers”. What are the parts of their day-to-day job where your candidate excels and stands out from the crowd? Ask for a live example, proven with numbers. Your CRO should know some parts of the job better than you, understand what you can learn from your new hire, and how it can be applied to your company priorities and business objectives.
• Numbers and attention to detail. I am a numbers guy, and you must excel in navigating performance tools and KPIs to have an excellent grip on day-to-day operations. That is to explore your top candidate’s experience with particular tools and understand what KPIs he/she had under control daily/weekly/monthly and quarterly. Ask for KPI’s inventory and discuss practical usage scenarios.
• Personality fit. You must surround yourself with people who can add new colors to your days. Imagine you will have to take a long flight with your CRO together; what will you talk about, apart from your job? Never make a C-level hiring decision from Zoom calls; bring your top candidate to town, take him/her out for dinner, and ask and learn as much as possible about their family, friends, hobbies, and interests. Talented people always have multiple talents. That’s a great way to understand your candidate’s values and life principles. Ensure the candidate’s values, communication style, and work ethic align with your company culture. A CRO who fits seamlessly into your organization’s culture is more likely to collaborate effectively with team members, understand your company’s mission, and contribute positively to its success.
• Leadership skills and charisma. Ask what makes your candidate a great leader and why the team will follow him. A CRO should inspire and motivate teams to achieve their goals while providing guidance, support, and mentorship. Assess their approach to decision-making, conflict resolution, and team empowerment.
• Player-coach. In many Sales organizations (particularly with sub $100M ARR), a CRO is expected to source and close deals — being a player-coach. Ask for live examples and repeat this question at your reference calls later.
• Cohesive Team Dynamics. Consider how the candidate will fit within your existing leadership team. Look for individuals who can complement the strengths of other team members and contribute to a collaborative and cohesive leadership environment. Assess their ability to work effectively with peers and support cross-functional initiatives.
• Hiring experience. Any great leader should take hiring (and firing) processes seriously and never delegate these decisions. Ask for live examples…
• Sense of humor. Yes, it’s a critical point for me. Personally, I have a dry, corky one myself. I use it a lot at my team meetings and to navigate difficult business situations. Having a sense of humor is indeed a critical trait, especially in high-pressure environments like sales leadership. It helps to make a hard day brighter and energizes the team.

6. Reference calls. Always do multiple ones. Do your research and make some unsolicited (contacts that your candidate has not shared with you) calls. Do it yourself, and don’t delegate this task to your HR/recruiter or an agency. Ask unexpected questions that will trigger non-standard conversations, so you will learn more about your new potential hire.

7. Having a mentor in your new CRO first 30–90 days. Ideally, a mentor should come from outside your organization. It can be a Board Member, Board Advisor, or an old Industry friend whom you can trust with this task. Make it formal and set an agenda as well as an expected outcome. Mentor will give you an extra and independent perspective on your new hire’s adaptation and performance.

8. Get ready with your new CRO onboarding plan. Usually, CEOs are too busy for that and expect that new CRO hire knows “how to swim”, so they will figure it out. Solid onboarding is critical to your new hire’s success — be available and get ready with a detailed agenda (with weekly deliverables tracking). Be careful, and don’t micromanage here.

Following these practical tips, you can make informed decisions when hiring your next CRO or VP of Sales. Remember, while Salespeople excel at selling themselves, assessing whether they’re genuinely the right fit for your business is essential.

Happy selling, and stay tuned for more sales strategy insights!