Your first
Data-to-AI hire

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About you

Ideal: Some product-market fit; seeing opportunities in product analytics or advanced AI/ML

Quick poll:

  • Name
  • Company
  • What are you hoping to learn?

About me

Helping climate & nature tech startups ship data-intensive solutions

Career highlights:

  • Software Engineering (BSc) / Data Science & Engineering / Artificial Intelligence (PhD)
  • 10+ years with startups & scaleups (after big tech)
  • 4× first Data-to-AI hire
  • Indie consulting: portfolio approach to tackling the climate & biodiversity crises

Main goal:
Avoid expensive mistakes

Cost of a wrong hire

COMPENSATION

+

SLOWDOWN

+

OPPORTUNITY

Sub-goals

  • De-hype Data & AI
  • Clarify needs & opportunities
  • Consider not hiring
  • Hire well
  • Avoid pitfalls

The lay
of
Dataland

Dataland: Venn's Paradise?

Startups
need not worry about
Dataland Venns

Ask de-hyping questions

Plumbing:
What's the state of your data engineering lifecycles?
Decisions:
How do you use descriptive, predictive, and causal modelling to support decisions?
Automation:
How do you use AI to automate processes?

Principles before tools

Some useful terms

Basic AI:
Black boxes like ChatGPT and transcription tools
Advanced AI/ML:
Custom models, harder, requires MLOps & serious data work beyond the prototype
Analytics:
The M in Build-Measure-Learn, key to product-led growth – depends on plumbing

OK, maybe one Venn...

Before
hiring

What do you need from Dataland?

  • Is it important for near-term growth?
  • List responsibilities, not titles
  • Make a 90-day plan
  • Define a successful outcome
  • Ensure everyone agrees

Consider not hiring

  • Do urgent work in-house?
  • Get a contractor / fractional?
  • Defer non-urgent work?

Achieving outcomes
without hiring
=
Massive win

Deciding
to
hire

Get even clearer on the role

  • 30 & 90 day plans
  • Aspirational goals for 6-12 month horizon
  • Likely level: mid-senior
  • Possible titles:
    • Data tech lead (analytics focus)
    • AI/ML lead (engineering focus)
  • Compensation isn't just salary + equity

Get help

  • (Good) recruiters are not the enemy
  • External recruiters: Help with sourcing and understanding the market
  • Internal recruiters: Help with the process and screening
  • Specialists: Help with technical screening
  • Remember the principal-agent problem

The hiring process

Run a process you'd love

  • Be clear and honest
  • Be responsive and efficient
  • Ask relevant, informative questions
  • Remember you're not Google

Sample process

  1. Ad: Clear & honest; include process, salary range, 30-90 day plans, and 6-12 month aspirations
  2. Simple call to action with custom questions
  3. Initial screen options:
    • Reject quickly and with note; or
    • Invite to 30-minute intro call
  4. Technical screen
  5. Final screen & offer

Relevant, informative questions

  • Derive from responsibilities and 90-day plan
  • Dig into past work and current motivations
  • Get techies to explain to non-tech staff
  • Technical screen:
    • Simple live screen questions
    • Take-home task
    • Dig into take-home response in call
    • Consider paid trials & contract-to-hire

Above all...
Keep it
efficient &
respectful

Avoid common pitfalls

  • Ignoring experts
  • Trusting the wrong experts
  • Google worship
  • Hunting unicorns
  • Expecting magic
  • Hiring narrow specialists

Recap: Key takeaways

  • Data & AI: Plumbing, decisions, and automation
  • Before hiring, get clear on your needs
  • Outcomes first: Consider alternatives to hiring
  • If hiring, run a process you'd love
  • Keep learning, get help, and avoid pitfalls

Story
time?

Car Next Door (Uber Carshare) 🚗

  • "Head of Data Science"
  • Opportunistic person fit, not a defined role
  • Plenty of engineering and analytics

Orkestra 📊

  • "Lead Data Scientist / Principal Technology Lead"
  • Started essentially fractional, morphed with time
  • Ambitious AI/ML work

...could have been a short contract?

Acknowledgements

Recruiter tips from: Mitch King, Eli Gündüz, and Matt Cook (they haven't reviewed the slides – mistakes my own).

First data hire tips from sources noted in my post on the topic.

Image sources: simple diagram, MLOps roles, Ryan Urbanowitz AI & Data, Jeff Winter AI, Matt Turck (MAD landscape), Andrew Bartholomew (Venn inspiration).

Questions? Feedback?

Logo and profile picture of Yanir Seroussi: Startup Data & AI Consultant
Happy to connect on
LinkedIn / Yanir Seroussi or via
yanirseroussi.com/contact/