Midnight Text: Closing the Critical CTO Hire

At Forum Ventures, we pride ourselves on really getting to know the founders we invest in, and creating (what sometimes is the only) space for them to drop their front and be vulnerable. As a result, we often get texts or calls in the middle of the night from our portfolio founders with urgent, confidential, and even sometimes what they feel are “embarrassing” questions. This series chronicles example founder texts and how we answer them.

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Alrighty, this one is critical. I don’t mean to scare you, but I want to be honest.  The reality is that a good CTO candidate will have other options, whether at other startups or for some cushy gig at a big company. And a good CTO can catapult your company to success, influencing the vision and attracting stellar engineering talent to your company. If you want to woo them to your startup, you need to do four things:

1. Learn what they want

Get to know your candidate as a person. Ask them about: 

• What kind of work they came from and want to move toward.
• What they loved and hated about their previous jobs.
• How they like to work: do they want to build a team? Manage freelancers? Handle strategy?
• Their interests in your space: do they have a personal connection to it in some way?
• Their life outside work: family, hobbies, interests, etc. 
• What makes them tick: Salary? Status? Impact? Upside? Work life balance? Meaningful contribution? 

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You’ll be surprised what you uncover as it relates to this person’s goals, wants, and needs, and you can tailor how you talk about your company and how the role can look accordingly. You will also win points with any candidate simply by caring about them as a person, And it benefits you: if they join, you’ll be spending a lot of time with this person, so you’ll want to use this time to get to know them better as well. 

2. Sell the vision

Once you know a bit more about them as a person, segue into talking about your vision for the company.

Sharing your vision is critical because not only will it inspire, it shows them where the company is headed and gives them a chance to visualize themselves joining you for the ride. 

The key to this step, however, is explaining the vision in terms of what this person wants out of life. For instance, if they talked about wanting to build a big team with multiple layers to it, explain your grand vision then talk about how you’ll need to build a strong team to get there. 

3. Sell the opportunity

After explaining the vision, dive into the specific CTO opportunity.

Share all the elements of the role that match what this candidates wants and needs. Some common ones are: building a team, building a worthwhile product that will help people, and having autonomy and trust to run their teams without interference. Also talk about your work style and how you hope to collaborate with this person as CTO.

When it comes to parts of the opportunity that don’t align with the individual’s goals, be honest. Your CTO (and any candidate, really) deserves to know the whole story so they can make an informed decision. 

And if the opportunity doesn’t match with what they’re looking for, consider tailoring it to align better. If they’re as strong a candidate as you think, they probably have a solid way of working that has driven success in the past … as long as it also aligns with what you need.  

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4. Remember to explicitly ask them to join

The final thing you must do is explicitly ask the candidate to join your company. Being wanted is a powerful feeling and can draw a candidate to you. Of course, this isn’t enough on its own - the opportunity needs to be a fit - but if you don’t close with an explicit ask, they may move on with the impression you weren’t sure. 

When you make the offer, be clear about what you can give them. Don’t promise salaries you can’t deliver on or work projects that may not materialize. Just be upfront with everything you can deliver on - then make sure you delive if they accept your offer.

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