Your First Sales Leader: Great Expectations or Great Results?

You’ve hired your first sales leader! You did all the references! You’ve closed deals and you’re not even a salesperson so this leader is going to be able to massively scale! Your VCs are thrilled!

Their 30-60-90 day plan was a masterpiece and you loved it. (Let me guess, the first 30 days was just listening.) If ANYONE has 100% fully stuck with their exact 30-60-90 plan please send it to me. By 90 days in, I’ve always had to tackle way more than the ‘people, process, tech’ I documented.)

And then….it didn’t work. Shockingly, you’re not the first person that’s been through this. I speak with quite a few founders and the stories are all worryingly similar.

Now, let's delve into a solution-oriented framework to ensure the success of your inaugural sales leader, or perhaps the first one truly tailored for your company.


  1. Are you hiring for the right role?
  2. Where do you look?
  3. Have you put in the work to ensure the interview elicits the right information for both parties?
  4. Are you setting this person up for success?
  5. How are you supporting this person ongoing?

Before anyone calls me out, yes there are exceptions. But for 80% of SaaS companies out there, I see founders wanting to run before they’ve mastered walking. Over-hiring is just as much of a problem (and often more expensive) than slightly under-hiring.

First: Have you spec'd out the right role?

‍Or in other words, do you really understand what you’re hiring for? You may want a CRO, but what do you actually need?

  1. Someone to work closely with the reps on the deals and be deeply involved in the full sales process?
  2. You expect a Forecast every week and for the person owning the forecast to be close enough to the deals to have credibility.
  3. This person to be solely focused on new ARR.
  4. Anticipating this person will plan only a few quarters out.

You need a VP Sales.

  1. This person will own the coordination of activity and KPIs between Sales, Customer Success, Marketing, Account Management? (note–there may be a CMO, I said coordination).
  2. They will be responsible for not just net new Sales but also Retention, Margin, Organisational Structure, Long-term Planning, Tech Stack and Channel/Partnerships?
  3. They will need to think about the overall GTM structure and playbooks that best suit the changing needs of your business?
  4. They will need to annual and multi-annual vision as to how the business should evolve in GTM, not just quarterly.

You need a CRO.

You can always promote a VP Sales to be a CRO. It’s really hard to convince a CRO that you need to demote the title and hire over them when the business needs it. If you really want a CRO but don’t need one just yet, hire a VP Sales with some KPIs to hit before getting that C-level title.

Second: Where do you start looking?

Hiring a senior sales leader is difficult, even when you know what you require.  You’ll need to determine which is more important: domain expertise or sales/stage expertise.  Then you’ll need to actually get access to these candidates, most of whom probably aren’t looking and aren’t familiar enough with your company to open an unsolicited message.  There are two main avenues to take here that I’d recommend:

  1. Speak with your investors.  Many VCs have dedicated Talent professionals who are constantly engaging with senior leaders both formally and informally. They’ll have a wealth of information about people perhaps not proactively on the market but who would make a great fit for your business.  
  1. Headhunting firms. An underutilised aspect of working with recruiters is that the best ones will be able to also offer perspective on sales professionals’ overall careers. You’ll find that many of the best firms aren’t just transactional here, they spend a lot of time building and nurturing long-term relationships and networks, and put a huge amount of investment and effort into their own events to upskill this network overall. This makes them deeply advisory to your business over the long-term and they can advise on candidates’ stage and gtm motion relevance. This approach also makes it a very easy way to get the attention of those who might not open emails from unknown internal recruiters. (Side-note, I often go to a few trusted recruiting professionals myself for advice on what types of roles and skill sets the top companies are currently focusing on, so I can make sure to benchmark my team’s performance and skills against the best.)
  1. Speak with other founders. Perhaps those ahead of you in the revenue journey.
  2. Speak to your customers.  Who from other vendors are they really impressed by?
  3. Industry bodies, such as Pavilion, Scalewise, Boardwave, etc etc?

Third: Have you set the right expectations in the interview process?

By this I don’t mean just telling the candidate what you expect. OF COURSE the VP from a big tech company who wants to get into a startup is going to say that yes, they’ll get involved deeply into every deal. Will they? Probably not. They’re probably used to managing other managers, and mostly getting deep into just the bigger deals. 

Please think about how you phrase the questions that you’re going to ask. Don’t just wing this. (See my previous article about hiring Sales Reps. Same principles apply)

If you expect the person to be very involved in deals and ask them if they will be, the answer will be yes. If instead, you ask for their vision of how the sales team will be structured, who does what, and how they envision the sales process working out from initial prospect contact through close to handover you’ll get a much better picture.

When you’re checking references, are you very specifically asking about the key competencies that are most important to you? Is this something that they’ve done in the past, something that they’re currently doing, or is it something that they haven’t done but the reference believes the person is capable of?

And, have you been brutally honest with the candidate about the product readiness and company situation? It’s absolutely fine to say that perhaps the product isn’t fully ready. It’s great to admit to certain aspects being a mess. Please share that you don’t yet have the marketing collateral sorted. Walking into a situation eyes wide open is a billion times better than going in with one set of expectations and being confronted with an entirely different reality. That doesn’t end well for either party and leads to resentment on both parts.

Fourth: You’ve had years to think of, sweat over, understand the nuances of your business. Have you documented these?

I’m a big believer that the CEO/Founders should be involved in the first deals. You need to understand how your product and vision resonate with prospects. You need to get an initial view on who the Ideal Customer Profile (ICP) is. You need to hear the objections.

It’s likely that you’ve been living with this company for at least a year, or years. There’s a lot of knowledge locked in your head that you don’t even realise. What’s intuitive to you, took a lot of trial and error to get there.

Please, document everything you can. This doesn’t mean writing playbooks–your VP Sales/CRO can do that. It means ensuring that you have an accessible record of what your customer interactions have been to date:

  • Common objections and how you’ve overcome these
  • Who tends to get involved in deals
  • Where you’ve failed in the past
  • What messaging you’ve used to date 
  • Use cases
  • Where/why customers have churned
  • How long deals have taken to close in the past
  • What steps had to occur in these initial deals
  • Product FAQs

A great VP will be able to use you as a very expensive Solutions Engineer initially then have this to run with as they enable the team to formalise processes. Then they’ll add to this, shape it and create frameworks and playbooks to standardise and create repeatability.

Fifth: Invest in a coach and/or mentor and training

You’ve just spent probably $£thousands to hire this person who will own the sales growth of your business. Spend a few more to support them.

For VP Sales, I’m a big believer (especially for smaller companies) in hiring for potential. I’ve seen time and again that given the chance, great Directors or Regional VPs have something to prove and will fight hard to swim up. But that also requires investing in them to support, train and mentor. Some of my best sales leaders were the ones who I took a chance on and either promoted or hired into a bigger role.

Who do you have in your network that you admire how they’re performing? Do your investors have access to other GTM experts that they can connect this person with?  Notion has a robust programme to provide access to other GTM experts, and I’m sure other VCs do as well.  Ensuring this person has access to other sales leaders to learn from, bounce ideas off and to hear new ideas that are working for others is a key driver of success.

Imposter syndrome is very real, for both men and women, especially when someone is taking on a big new role, which this will be for them. Getting a coach to help talk through it can be extraordinarily helpful. I’ve had HR leaders say that they’re a qualified coach, and didn’t understand why I was reluctant to have my newly promoted sales leaders speak about their insecurities and weaknesses with the head of HR. I’ve also had HR send out messages about offering coaching, then a few weeks later an email to confirm that nothing said was to be considered confidential. Shockingly, the takeup dropped off. Get a coach or a mentor entirely outside of the company so there can be real conversations please. This will help your sales leader think bigger, gain strategies to deal with the stress of leading revenue and ultimately be a happier and more productive leader.

Investing in training is also a no-brainer, that I see often for ICs but rarely for management. Sales coaching isn’t always intuitive–asking for details of close dates, value, probability isn’t coaching, it’s a pipeline review. This is an investment that always pays off—and is so rarely offered.

In sum: 

I hate to say this but success often hinges on the founder’s preparedness. Why did it go wrong? The candidate was hired for the wrong role, they had an entirely different expectation of what they were walking into, or they weren’t set up for success.

I can’t guarantee that your next-first-sales-leader will knock it out of the park, but hopefully you’ll at least not hire that candidate that never had a chance.

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