The senior-most technology focused executive at a tech startup is a make-or-break hire. They set the technical vision of your product based on feasibility and ambition. At the seed stage this person will create the first version of your product and iterate until you achieve product-market fit. During the growth stage this individual will be responsible for the majority of your raised capital in the form of engineering headcount. Across all stages your CTO may be the difference in the race to deploy effective AI for your customers or a successful hardware launch. And like any executive they should make everyone else better at their jobs.
Your CTO will also set the culture of your product development org for years to come. This might be the largest long-term impact a CTO makes. As you grow, their hires hire their own team members and this influence proliferates. Grade A leaders attract and hire grade A talent (see Vinod’s blog Gene Pool Engineering for Startups and The Art, Science and Labor of Recruiting). And great talent seldom join a team they are not impressed by and want as peers. Great engineers don't want to be interviewed by "ok" engineers–they want peers they can learn from. This permanently impacts the capability of the organization for years–even after the leader has moved on.
Many first-time founders understandably don’t have the necessary functional knowledge or previous work experience to assess, close, and manage a CTO with a high-degree of confidence. So at Khosla Ventures, in keeping with our Venture Assistance model, we provide help and support to founders to make amazing, high-impact hires.
| "Khosla Ventures was exceptionally helpful on our CTO search, introducing us to stellar candidates, interviewing top contenders, and providing valuable technical feedback. Vinod personally met with all our finalists and helped us close our top pick. 🐐 A+ support and hustle from start to finish." – Jonathan Swanson, Founder of Athena & Thumbtack |
Our KV Talent team is fully staffed with senior, experienced recruiting leaders. They maintain a list of vetted, active candidates called “Candidates in Orbit”. They will review hiring assets, provide feedback on the interview process, assess candidates, make intros, share compensation benchmarks, and maintain relationships with partners at the top executive recruiting firms.
Additionally our Operating Partners are available to interview your finalists. Operating partners are previous executives at successful, high-growth startups who leverage their backgrounds including in Engineering. Once a candidate accepts and starts our operating partners continue to be available as advisors to help ensure a successful onboarding and a long impactful tenure.
Decide What You’re Looking For
The CTO position is one of the most varied executive decisions at a startup. So it’s important to plan your org chart so you know exactly what responsibilities you need in a CTO. You may actually need a Head of AI or VP of Engineering. There are several common patterns. The most straightforward scenario is you are looking for a hands-on technical cofounder, or a Head of Engineering that reports directly to the CEO. They might head AI for you, or delegate it to a specialist. Product management typically sits outside this person’s responsibility.
- CEO
- Head of Engineering (CTO or VPE title)
- Head of AI
- Head of Product (perhaps the CEO)
- Head of Engineering (CTO or VPE title)
The second scenario is similar except you already have a founding CTO who created the first version of your product but doesn’t want to become more managerial or take on additional executive responsibilities. They still provide impact by staying highly technical and perhaps run a small team working on prototypes or high-impact areas such as AI. In this case you may hire a VP of Engineering. The CTO title might also be reserved for an AI-focused practitioner in this case.
- CEO
- CTO (...or…)
- Head of Engineering (VPE title)
- Head of Product
- Head of AI
Increasingly (~15% of the time) we see CEO/founders looking to delegate all of product development to one executive who needs to be skilled balancing customer relationships and what needs to be built (prioritization) with how the product is built (engineering). The Chief Technology & Product Officer (CTPO) title is the most descriptive for this role and they typically have functional heads reporting up into them. They also likely own design.
- CEO
- CTPO
- Head of Engineering
- Head of Product
- Head of Design
- Head of AI
- CTPO
You may choose to use the future-proof “Head of Engineering” label if you feel your company’s needs are growing faster than people can reasonably scale. This would allow a seed stage startup to hire someone with Director-level experience from a larger company with the flexibility to hire over them in 2-4 years when they reach their limit. Converting their title to Director or VP is far less painful than demoting them, which increases the likelihood that someone leaves due to having lost face. It’s important to be transparent about possible outcomes during the closing process to ensure no one feels misled. To this end always advertise the lowest acceptable title publicly–you can always negotiate up from there.
CTO Criteria
The primary artifact that anchors a hiring process is the job description even if the job is never advertised publicly. A good job description should inform candidates (and everyone involved in the hiring process) about the company, let them know the scope of the role, list the desirable qualities of a good fit, and outline what a successful hire will accomplish in their first year.
Don’t over-specify the role as some candidates may self-censor and choose never to apply. You also don’t want to ‘teach the test’ to clever candidates who don’t have the necessary experience but are articulate enough to speak about things that happened around them. Let candidates know what you are looking for without disclosing exactly how you will assess it.
Ask our talent team for examples of great relevant job descriptions you can start from. In the meantime here are some criteria you’ll want to include:
- Stage Appropriateness
- Have they worked at your current stage, and helped grow a company to the next stage?
- Can they build the first version of your product and help you attain PMF (seed stage)?
- If they’ve never worked at a startup before, are they exclusively considering startup roles?
- Can they hire, manage a team, provide project status, and improve product quality and security (growth stage)?
- Technical Credibility
- Hands on
- How hands-on are they? Are they able to set up the development environment, occasionally work on bugs and small features (nothing critical path)?
- Do they have past evidence of challenging technical work?
- Technical vision
- What languages/frameworks do they advocate for?
- How do they run a buy/build decision?
- Can they take part in architecture discussion and correctly evaluate proposals?
- Experience with AI/ML
- What was the business impact of the models they got into production?
- Have their teams worked on state-of-the-art generative AI? (tokenization, fine-tuning, RAG, vector databases, et cetera)
- What pre-LLM technologies have their teams deployed? (regression, boosted trees, GANs)
- Hands on
- Hiring Great Engineers
- Where do they set the bar?
- How do they attract superstars?
- How do they partner with internal and external recruiters?
- How do they conduct technical evaluations?
- Have they experienced hyper-growth?
- Who makes the hiring decision?
- People Management
- How do they motivate people?
- How do they manage performance?
- How do they help engineers develop their careers?
- Project Management
- How do they communicate status and predictability to stakeholders?
- How do they keep the process efficient?
- How do they manage AI/ML projects where progress can be non-linear and the outcome cannot be predetermined?
- What project management frameworks have they employed in the past?
- What specific systems do they favor?
- Product Quality
- How do they know what the quality of the software is that their teams are shipping?
- If it’s below some bar, what do they do about it?
- What types of tests are being written, and who is writing them?
- Product Security
- How do they justify the appropriate investment in security?
- How do they assess risk?
- What sorts of security activities have they managed?
Some important criteria cannot be evaluated by directly asking questions. Instead you must give candidates the opportunity to demonstrate these qualities.
- Mission Fit
- What motivated them to apply?
- If [our company] didn’t exist what would you be doing next?
- Does your company’s mission address some challenge the candidate has experienced in their work or personal life?
- Keep in mind that mission fit can develop over the course of a candidacy and may not be evident during the early interviews
- Communication Style
- Allow candidates to respond to some questions in long form, perhaps a business challenge with a counter-intuitive solution, or the story of their tenure at their most recent company
- Can they effectively summarize obscure technical information to people not previously familiar with the topic?
- Consider the candidate’s communication with the recruiting team a proxy for how they work cross-functionally and asynchronously
- Humility
- Do they often say ‘we’ instead of ‘I’
- Do they take the time to recognize team members as their highlight previous accomplishments
- Do they avoid excessive criticism of previous stakeholders?
For more on selecting criteria see Vinod’s article How to Hire a CEO, much of which applies to CTOs.
Use an Executive Recruiting Firm
Many founder’s initial instinct is to go it alone, try to recruit themselves, and save the money that would go toward recruiting fees. Or sometimes they think an early stage cofounder is not an executive position and they will only see candidates who manage hundreds of engineers and don’t code. It’s important to understand that the best executive recruiting firms provide the following:
- They already have relationships with top candidates because they placed them in past roles.
- They provide an excellent candidate experience that is quite often the differentiator for a startup competing in a crowded marketplace, sometimes against larger tech companies with higher cash offers.
- They buffer the negotiation over compensation, ensuring a win/win agreement so everyone is feeling positive going into the start date and onboarding.
- A much higher volume of quality candidates (up to 5x), which helps with calibration.
I recently helped one of our portfolio companies by interviewing CTO candidates in the third stage (after an in-house recruiter and CEO but before the team onsite). I interviewed 15 candidates with a pass rate of 27%, which remained steady over the process. No candidate received a ‘strong yes’ during this period. Once we decided to use an executive recruiting firm I interviewed another 13 candidates with a pass rate of 46%. More importantly the agency calibrated and improved their results steadily culminating in 3 of the final 4 candidates passing, one of whom received a ‘strong yes’ and accepted the offer. Thankfully we never lowered our bar, but in retrospect partnering with a firm would have more than halved the time needed to fill the position.
Talk to our KV Talent team about what partners they recommend at which firms. They will also be available to augment these firms so founders know they are being treated fairly and that the right activities are happening to lead to a high-quality, timely hire. Founders should still expect to be very involved in the sourcing process as they will get the highest response rates by using their own identity, especially for passive candidates.
Interview Stages
A hiring process is a heuristic. You have on the order of hours to determine whether you want to work with someone for years. And hiring a senior role means entrusting them to act on their instincts to get business results, while being transparent about their strategy and the current state of work.
Keep the process as symmetrical as you can from candidate to candidate. Don’t skip any steps, but don’t make the process overly long either. One of the key ways that startups can compete with large tech primes with high-cash offers is the speed of their decision making.
- 30 minutes: Recruiter Screen
- Assess high-level criteria
- Stage appropriateness
- Mission fit
- Communication style
- Humility
- Align on compensation expectations
- Ensure candidate interest
- Assess high-level criteria
- 30 minutes: Hiring Manager (CEO)
- Assess high-level criteria
- Stage appropriateness
- Mission fit
- Communication style
- Hiring
- Humility
- Project management
- Assess professional compatibility and whether the candidate is a positive cultural addition to the company
- Build interest, excitement, and momentum for the rest of the process
- Assess high-level criteria
- 60 minutes: Quality Control (an Advisor)
- An opportunity for a functional expert to keep the bar high
- Identify strengths and weaknesses for further evaluation at the team onsite
- A high-speed pass over all the criteria to catch exceptions
- Half-day: Team Onsite
- 60 minutes: A coding exercise
- Criteria: Assess technical credibility (Hands on, AI)
- Use the same exercises you use for individual contributors
- Expect some rust from growth-stage CTOs
- Alternatively consider a take-home exercise
- 60 minutes: An architecture exercise
- Criteria: Assess technical credibility (vision, AI)
- Work through a recent or imminent problem facing the system
- Use the same prompt for all candidates to allow for comparison
- 60 minutes: A culture fit interview with an engineer
- Criteria
- Hiring
- People management
- Project management
- Security
- Quality
- Criteria
- 60 minutes: A peer interview (usually product management)
- Criteria
- Communication style
- Mission fit
- Project management
- People management
- SDLC
- Balancing tech debt and features
- How engineers maintain their customer empathy
- Criteria
- 60 minutes: A coding exercise
- Half-day: Working Session with Founders
- Work through a real, upcoming business problem
- Use the same prompt for all candidates to allow for
- The meeting should start structured, but be flowing toward the end
- Social / Anecdotal
- Dinner/drinks with the exec team to understand life/family/interests, et cetera
- Reference Checks
- Offer
You can customize this template in a variety of ways. You can increase the number and intensity of technical evaluations based on your needs. You can also move the quality control interview to the back of the funnel if you have limited bandwidth from advisors.
Require that interviewers supply prompt, written feedback on each aspect of the criteria they are supposed to cover for the group. Identify backup interviewers for each stage so you don’t block on availability. Ask them to provide an overall recommendation on the scale of “strong no”, “no”, “maybe”, “yes”, and “strong yes”. Perform a team tag-up meeting coming out of the onsite to discuss feedback and calibrate. Encourage interviewers to come down on a firm opinion and avoid “maybe”. A “maybe” should be a “no” once you are calibrated as a team.
Involve your team as much as possible in the selection of their future leader. Be aware it’s common for individual contributors to underestimate the value of an executive role and to be inexperienced assessing for it. You might get the interview feedback “why don’t we just hire another engineer to write code?” while at the same time lamenting about hiring quality, too much tech debt, poor uptime or other topics engineering management usually solves.
Don’t waste anyone’s time, but be a little liberal early in the process to make sure some candidates make it to the onsite stage. It’s worth the time to calibrate on the changing future needs of your company. But reinforce that the CEO makes the final decision as hiring manager.
Interview Shadowing
If you check beforehand with the candidate it can be helpful to have the hiring manager shadow the interview conducted by one of our operating partners. Watch them type notes live in a shared document so you can get a sense of how they interpret the information you’re both hearing from the candidate. Pay close attention to how and when they ask followup questions to press on certain criteria. It’s usually advisable for the shadow to stay reticent so it doesn’t feel like a panel interview. It also doesn’t hurt to ask whether the meeting can be recorded so it can be confidentially shared with the rest of the interview team.
Reference Checks
While reference checks have fallen out of favor somewhat as outdated and time consuming, they are still immensely useful in two main respects:
- Learning how to best set up any candidate up for success as their new manager
- Filtering out the rare bad fit who made it deep into your process who nevertheless may have a track record of poor collaboration in their prior working environments (bad hires can cost an organization 3-5x their annual salary accord to a study by the Society for Human Resources Management)
Get several manager references, and at least one peer and one direct report for a 360 degree view. Great candidates will have very impressive references speak on their behalf. Seek out back door references, but be sensitive to confidentiality in case the candidate has not disclosed their departure to their current company. A back door reference can be assessed more on face value. A front door reference needs to be over-the-top to be considered positive, such as:
- “This person was the best boss I ever had!”
- “This person made everybody on the team better!”
- “I was so sad to lose this person when they moved on!”
The hiring manager should conduct their own reference checks and not delegate to a recruiter. Here is a script that can be covered in 15 minutes. Remember that any touch point with someone outside your org is an opportunity to impress and create an ally.
- “Thanks for taking the call. I appreciate the time. Anything you share will be kept confidential between us.”
- “What was your relationship to the candidate?”
- Which company?
- For how long?
- What was your role?
- What was their role?
- Who did the candidate report directly to?
- Did the candidate report directly to this person?
- Yes
- “What were the candidate’s major achievements?”
- “What did the candidate work on improving with you during your time together?”
- No
- “What are the candidate’s strengths?”
- “What are the candidate’s weaknesses?”
- Yes
- “Would you work with this person again? In what capacity?”
- “What percentile (e.g. 25th, 50th, 90th) is this person amongst everyone you’ve worked with” or “Where would you stack rank this person on their team?”
- “What does this candidate need from their manager to be successful?”
- “Is there anything else I should have asked that you think I should know?”
- “Thanks for your time! Don’t hesitate to reach out if I can ever be helpful in answering a question, making an intro from my network, or something else.”
Be effective with this person’s time, represent yourself and your company well, and offer to reciprocate. The tech world is small. But also you may wish to hire the person giving the reference one day!
Closing your Top Candidate
Keep in mind that candidates are assessing you and your company as you assess them. Every interaction is an opportunity to win or lose a superstar. Don’t forget to build excitement and momentum throughout the process. Learn what motivates your candidates and make sure they come to see the impact they will have on your company. At the same time, don’t get lost in the sale and lose sight of your assessment.
Partner with your executive recruiter on the timing and content of the offer, but deliver it yourself. Demonstrate your excitement for this person to join your company. Take the time to highlight specific characteristics that allowed them to stand out from the pack.
You should already be within 15% total compensation (base, optional bonus, and equity) if all sides have done their homework and been transparent. Do not be offended you do not get an immediate ‘yes’ as job changes are one of life’s few major life changes and considerate individuals like to take their time making decisions. But do expect a timeframe for a final decision.
Also don’t be offended by a reasonable counter-proposal. You are hiring a leader who must be comfortable negotiating hard on behalf of your company with candidates and vendors after they join. Common discussion points are stage dependent, but can include:
- Double trigger RSUs
- Post termination exercise window
- Accelerated vesting
- Early exercise
- Signing bonus
- Incentive/milestone-based annual exec bonus
Afterwards, encourage members of the interview team, fellow executives, and investors to reach out to the candidate to congratulate them on receiving an offer to join. This demonstrates a welcoming atmosphere, and also a degree of organizational alignment and coordination that will indicate to a candidate they are joining a well-run team.