AI Transformation Lead

Company shown to members 🔒 · Remote · US, Canada only

US, Canada only5+ years requiredPublished 21 October 2026Looks fresh

Apply free: 3 jobs are on us✨ Tailor my resume for this job🎤 Practise the interview question, free

✓ Straight from the company's own careers page. No middlemen, no “we'll send you a check for equipment”. How we check jobs

✓ Sent 100 applications and heard nothing? Make this one count: tailor your resume to this ad in one tap, free.

✨ Not sure this is the one? Get your remote job matches in 30 seconds →

First recorded by Psst: 22 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.

Free interview practice

Practise the first interview question for this job

If the company replies, the first call usually starts with a question like this. Vague answers are the easiest to reject. Write yours and get an AI score in under a minute.

The 20-second read

Experience
5+ years required
Where you can live
US, Canada only
Skills and tools
sql, saas, documentation
Job type
Full-time

Read from the ad by Psst's rules. Check the full ad below before applying.

Job details

Where you can work
United States, Canada
Employment type
Full-time
Advertised pay
Not stated by the employer
Experience
5+ years required
Employer publication date
21 October 2026
First recorded by Psst
22 October 2026
Last checked at the source
10 November 2026

About the job

At the company, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands - we need to try to help small businesses and creative individuals too.

You will be the strategic and technical owner of transformation engagements on a defined set of accounts. The most informed voice on what the company should do for each client and how the work gets done. You set the thesis, structure the engagement from first principles, co-design the recommendations and timelines with Forward Deployed Engineers and Creative Leads, lead the client through the enterprise-wide change required to make it stick, and stand behind quality and performance once the work ships. You own the recommendations and the narrative we tell our clients.

Candidates must be based in North America and have consulting and/or agency experience to be considered for this role.

Key responsibilities

  • Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan that drives the engagement, setting the transformation thesis, co-designing the recommendations with Forward Deployed Engineers and Creative Leads
  • Structured Problem-Solving: Take ambiguous client problems and structure them from first principles into a clear set of hypotheses, workstreams, and sequenced decisions everyone can act on.
  • Change Management Leadership: Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows - navigating complex stakeholder landscapes, identifying blockers and champions, and engineering the buy-in that scaled AI adoption requires.
  • AI Process Design: Translate abstract GenAI concepts into clear, repeatable operating processes that client teams can execute confidently day-to-day.
  • Product Feedback Loop: Act as the voice of the customer internally, feeding insights back to Product and Engineering - what's missing, what's broken, what's worth doubling down on - so the company's roadmap stays enterprise-ready.
  • Transformation Blueprints: Codify what works on your accounts into repeatable Blueprints the rest of the team can run, so every successful engagement leaves behind a sharper playbook than the one before it.

Your background

  • Minimum of 5 years’ experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations. A strong academic record in a quantitative or analytical discipline is preferred.
  • AI-native in your day-to-day. You already use Claude Cowork; experience with Claude Code or other agentic tooling is a strong plus. You don't wait to be told to automate something.
  • Tech-fluent and hands-on. You're in the the company platform yourself - configuring agents, prototyping, stress-testing recommendations - and you can hold your own in a technical conversation with a client's engineers about their stack. Lightweight engineering - SQL, scripts, reading code - is a strong plus.
  • Confident with senior stakeholders. You can carry a client meeting on your own, give direct feedback, and stay composed when scope shifts.
  • A track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time.
  • Marketing, advertising, or agency experience is essential for this role.

You’ll Thrive Here If You…

  • Are Provocative and Brave: You aren't afraid to challenge a customer’s existing way of working if it means helping them avoid long-term implementation challenges.
  • Are an Ally to Change: You are comfortable with ambiguity and change, and you take pride in being a trustworthy partner who helps others navigate the "new and unknown."
  • Believe in Enterprise Adoption: You are obsessed with seeing technology move away from “pilot purgatory" and towards an embedded, value-driving part of a company’s culture and success.
  • Embody the company Values: You lead with transparency, agility, and a focus on measurable impact, ensuring our values are mirrored in the customer’s own transformation journey.

KPIs & Success Measures

  • Enterprise Adoption: Depth and breadth of the company usage across a customer's teams, departments, and use cases once the rollout is live.
  • Time-to-Value: Speed at which your accounts reach their first defined success metric or ROI milestone after engagement kickoff.
  • Quality of Transformation Narrative: How well your transformation thesis and the strategic and tactical planning survive delivery without major rework, and the performance the recommendation drives for the client post-launch.
  • Product Feedback Impact: Quality and reach of insights fed back to Product and Engineering that keep the company's roadmap enterprise-ready.
  • Blueprint Contribution: Successful documentation and internal adoption of repeatable "Transformation Blueprints" based on customer wins.

Benefits

  • 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme
  • Health insurance / private medical cover
  • Monthly stipend towards wellness, fitness, and learning and development
  • Remote - work from anywhere in your home country
  • Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy
  • Access to our the company office in The Shard, London for UK employees
  • Flexible working hours

Apply free: 3 jobs are on us✨ Tailor my resume for this jobPrepare with the Apply kit

Find my remote job matches →
Ghost Job Detector: Looks fresh
  • No pay listed
Signals, not proof. Check the company's page before you spend time on it.
Free to build · no sign-up

A resume that gets past the first 6 seconds

Recruiters skim. The Psst resume coach fixes what makes them skip you, line by line, and one tap tailors it to the exact job you're applying to.

  • 1Every line checkedWeak starts, clichés and AI-sounding phrases flagged, with a 3-question fix.
  • 2Tailored to the jobSee which skills and tools from the ad your resume is missing. Try it free on one of your matches.
  • 3Ready for remoteTime zone, tools and proof you work on your own, the things remote teams look for.
  • 4Looks the partOne page, 6 designs, 8 colours and a matching cover letter, free to build. Premium downloads the PDF and Word files.
Try the resume coach →Compare Premium

Set up your job alert