Advisory Lead, AI Transformation

Role Type: Remote, attending in-person client meetings as needed
Role Location: North America

Core Hours: EST Timezone

What is the opportunity?

Bold AI is scaling its advisory practice to help clients realize meaningful productivity, automation, and revenue outcomes through AI-enabled transformation. We are seeking an Advisory Lead, AI Transformation to lead high-value client engagements from opportunity origination through delivery. This role combines strategic advisory, executive-level program leadership, and hands-on oversight of the cross-functional resources required to turn transformation ambitions into delivered results.

Who you are:
You are a technologist who learned to sell, or a strategist who learned to build. Either origin story works. What matters is that you can sit with a CFO in the morning and shape a value case, then sit with an engineer in the afternoon and make a real architecture tradeoff. Not translate between them, make the call yourself.

You have run delivery where the outcome was working with software, not a recommendation. You are comfortable being the most senior technical person in the room and the person who owns the outcome.

You want the scope that comes with a small team. That means you write your own proposals, run your own discovery, and stay close enough to the build to know when it’s off track.

What you’ll own:

• Solutioning and pitching:
  Shape client ambition into scoped, priced, defensible engagements across custom builds, AI implementation, and workflow automation. Lead the executive conversation, build the value case, and close the work.

• Lead delivery:
  Own execution end to end once the work is sold. Set the technical approach, sequence the build, and uphold the quality standard. Engineering reports into this role, so team direction, capability planning, and prioritization will sit with you.

• Expand the work:
  Turn one-off engagements into repeatable offers. Identify which client use cases deserve to become productized assets and drive them from prototype to shipped marketable products.

• Grow the team:
  Define the capability mix as the discipline scales, then hire and develop against it.

• Own the commercials:
  Accountable for revenue, delivery margin, and client retention alongside the leadership team.

What you bring:

• 8+ years across technical consulting, engineering leadership, or digital product delivery shipping production systems for external clients

• Hands-on depth in modern build work: application architecture, APIs and integration with legacy systems, cloud infrastructure, and full SDLC. You should be able to read a pull request and have an opinion.

• Practical experience implementing generative AI and agentic systems into production including automation and workflow orchestration. Pilot-only experience will not carry this role.

• A track record of originating and closing work. Scoping, pricing, proposal writing, and executive presentation, not just delivering what someone else has sold.

• Experience managing engineers directly, including performance, capability development, and resourcing across concurrent engagements.

• Comfort building the operating layer. We have delivery methodology and proposal foundations in place. You will inherit them, mature them, and set the standards we run at scale.

Where the role fits in the organization:
This is a key role in Bold AI’s AI Transformation group. As the discipline scales, the intended path is Practice Lead, AI Transformation with full accountability for the P&L, the team, and the offer portfolio. We’re evaluating for that trajectory, not just the current scope.

What’s in it for you:
You get to shape how a growing firm delivers AI transformation, with direct access to engineering and the autonomy to originate and close meaningful work. You're not starting from a blank slate, there's live client work waiting. You'll report directly to our co-founder, which means short decision cycles and no layers between your judgement and the outcome.