INDUSTRIES
Technology and AI leadership search
Tech companies are cutting in some places and fighting for talent in others, and AI has changed what a strong leader looks like in almost every function. Here's what makes each leadership search hard right now, what to look for, and what to watch out for.
The market right now
- (CompTIA, September 2026)
- (McKinsey, August 2026)
- (IBM, May 2026)
- (SignalFire, May 2025)
Leadership roles we recruit
In demand now
- Head of Forward Deployed Engineering
- VP of Solutions Engineering
- Head of AI Governance
- Head of AI Security
- AI Product Lead
- Head of AI Platform and FinOps
- Head of Developer Relations
Role guides
CEO and President
- Why it's hard right now
- Many external tech CEO searches follow an unplanned transition, so there is rarely a clean template for the role.
- What to look for
- Experience at your stage and revenue range. Has led a company through a product or platform shift. Strong with boards and investors. Grows efficiently with a lean team.
- Watch out for
- A large-company executive stepping into an early-stage company without a plan for the change. An AI story with no product or revenue result behind it. A pattern of stints under three years.
CTO, VP of Engineering and Engineering Managers
- Why it's hard right now
- Engineering leaders are being asked to deliver more with AI and smaller teams. 73% now rank managing AI agents as their top skill priority, and 54% of CTOs say they feel emotionally drained every week. (LeadDev, June 2026)
- What to look for
- Evidence of how AI changed their team's delivery, with reliability numbers, not just speed. Google's DORA research found AI hurts delivery stability unless testing and version control are strong (Google DORA, September 2025). A record of building teams, and credibility as a hands-on player-coach.
- Watch out for
- "AI made us faster" with no reliability data. Leaders who were only effective with a large platform organization around them.
- Pay data
- The BLS median for computer and information systems managers is $175,140 (May 2025).
Chief AI Officer, Head of AI and Head of Machine Learning
- Why it's hard right now
- The title means very different things at different companies. Estimates of how many large organizations have a Chief AI Officer range from 38.5% (Data & AI Leadership Exchange, December 2025) to 76% (IBM, May 2026). Frontier AI labs have also pushed pay expectations to extremes.
- What to look for
- AI in production with measurable business impact. MIT research found only about 5% of custom enterprise AI tools reach production (MIT NANDA, August 2025). Also look for evaluation discipline, data readiness and governance, and sound build-versus-buy judgment.
- Watch out for
- A portfolio of pilots and demos. A research profile for an applied role, or the reverse. A relabeled title with no real scope.
- Pay data
- At startups, median AI and machine learning engineer salary rose 9.1% and median initial equity grants rose 31% from January 2024 to February 2026. (Carta, May 2026)
VP and Director of Product
- Why it's hard right now
- There are more than 7,300 open product manager roles, the most since 2022, and demand for AI product managers is climbing fastest. (Lenny's Newsletter with TrueUp data, March 2026)
- What to look for
- AI features shipped with measured adoption. Comfort with evaluations and unpredictable model outputs. Pricing and packaging experience. Awareness of inference costs.
- Watch out for
- Roadmap owners who manage process but not outcomes. "AI product" experience that was only a thin wrapper around a model.
Chief Data Officer and Head of Data
- Why it's hard right now
- 70% of chief data and analytics officers now own AI strategy (Gartner, May 2025), and 93.2% of large enterprises say culture, not technology, is the main barrier to AI adoption. (Data & AI Leadership Exchange, December 2025)
- What to look for
- AI-ready data (quality, lineage and governance) tied to AI that actually shipped. The ability to measure business value. Influence with executives.
- Watch out for
- Governance-only profiles. Platform builders who can't point to business results.
CISO and Head of Security
- Why it's hard right now
- 59% of organizations report critical or significant security skills gaps, and AI is now the most-needed security skill. (ISC2, December 2025)
- What to look for
- AI and agent security, board-level communication, cloud security depth, and leadership through real incidents.
- Watch out for
- Checklist-compliance leaders without engineering credibility. Tool buyers.
VP of Infrastructure, Platform and DevOps
- Why it's hard right now
- 90% of organizations have adopted at least one internal platform, and platform quality now decides how much value AI delivers. (Google DORA, September 2025)
- What to look for
- Runs the platform like a product with developer-experience metrics. Reliability targets and discipline. Owns cloud and compute costs. GPU and inference infrastructure for AI companies.
- Watch out for
- Tool-first thinking. No cost accountability. Experience only at hyperscale.
Chief Revenue Officer, VP of Sales, CMO and VP of Customer Success
- Why it's hard right now
- Growth now has to be efficient, and marketing leaders face new AI expectations. Gartner predicts that by 2027, weak AI literacy will be one of the top three reasons CMOs are replaced. (Gartner, February 2026)
- What to look for
- Efficient-growth metrics such as net revenue retention and CAC payback. Experience selling usage-priced or AI products. Customer Success leaders who own expansion revenue.
- Watch out for
- Results that depended on 2021-era budgets. Quota claims you can't verify. Marketing leaders who hand AI off to their teams.
Founding, Staff and Principal Engineers
- Why it's hard right now
- AI and machine learning is now one of the best-paid tracks in engineering, and early-stage teams are small, so every senior hire carries more weight.
- What to look for
- Systems built from zero to one, end to end. Good judgment using AI coding agents. Product sense. Strong written design leadership.
- Watch out for
- Inflated titles. Specialists who need a lot of support around them. Candidates who can't separate their own work from what AI tools produced.
How TAP runs this search
We start with an intake that goes deeper than the job description, then map who is doing this job today at companies like yours, including leaders who aren't looking. Every candidate is interviewed in depth before you meet them, and you get a private website on each finalist: interview video, a rating on each of your requirements, compensation, timing and why we recommend them. Our goal is your hire from the first two candidates we present.
Hiring for one of these roles, or want a second opinion on how to recruit for it?
Across our careers, we've recruited for roles like these. Tell us what you're hiring for and we'll share what we'd look out for, whether or not you start a search with us.
Frequently asked questions
- Most of our searches take 4 to 10 weeks, depending on the role and the market. Senior AI searches can take longer when the pool is small.
- Yes. Most companies don't need a frontier researcher. They need a leader who has put AI into production and tied it to business results. That's the profile we focus on, and it's a much wider pool.
- 25% of the new leader's first-year compensation. On most packages, an engagement fee paid at the start is credited toward it, and the placement fee is invoiced on your new leader's start date. See the full fee guide.
Sources
- CompTIA, tech jobs analysis, September 2026: https://www.prnewswire.com/news-releases/technology-occupations-grow-across-us-economy-despite-staffing-pullback-at-tech-companies-comptia-analysis-reveals-302870145.html
- McKinsey, The State of AI, August 2026: https://www.mckinsey.com/capabilities/quantumblack/our-insights/the-state-of-ai
- IBM CEO Study, May 2026: https://www.stocktitan.net/news/IBM/ibm-study-ce-os-are-reshaping-c-suite-roles-for-the-ai-mzin3bnnfjld.html
- Carta, startup compensation report, May 2026: https://carta.com/data/startup-compensation-h2-2025/
- SignalFire, State of Talent Report, May 2025: https://www.signalfire.com/blog/signalfire-state-of-talent-report-2025
- LeadDev, Engineering Leadership Report 2026, June 2026: https://leaddev.com/wp-content/uploads/2026/06/ENGINEERING_LEADERSHIP_REPORT_2026_FINAL.pdf
- Google DORA, 2025 report, September 2025: https://cloud.google.com/blog/products/ai-machine-learning/announcing-the-2025-dora-report
- Data & AI Leadership Exchange, 2026 AI & Data Leadership Executive Benchmark Survey, December 2025: https://static1.squarespace.com/static/62adf3ca029a6808a6c5be30/t/6942c3cb535da44088c2dbff/1765983179572/2026+AI+&+Data+Leadership+Executive+Benchmark+Survey+Final.pdf
- MIT NANDA research via Virtualization Review, August 2025: https://virtualizationreview.com/articles/2025/08/19/mit-report-finds-most-ai-business-investments-fail-reveals-genai-divide.aspx
- Lenny's Newsletter, state of the product job market, March 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9
- Gartner, chief data and analytics officer survey, May 2025: https://www.gartner.com/en/newsroom/press-releases/2025-05-12-gartner-survey-finds-seventy-percent-of-cdaos-are-responsible-for-artificial-intelligence-strategy-and-operating-model
- ISC2, 2025 Cybersecurity Workforce Study, December 2025: https://www.isc2.org/Insights/2025/12/2025-ISC2-Cybersecurity-Workforce-Study
- Gartner, CMO survey, February 2026: https://www.gartner.com/en/newsroom/press-releases/2026-02-23-gartner-survey-reveals-cmo-ai-blind-spot-as-65-percent-expect-role-disruption-yet-only-32-percent-say-significant-skill-changes-are-needed
- BLS Occupational Outlook Handbook, computer and information systems managers: https://www.bls.gov/ooh/management/computer-and-information-systems-managers.htm
Last reviewed September 2026