Deployment Strategist

The Role

You bring AI into commercial insurance brokerages and own that transformation end to end, from the kickoff to measurable adoption. Herald is the placement system for the commercial insurance middle office: industry-specific AI that reads emails, extracts data, generates quotes, integrates with carriers, and guides brokers through submissions.

You will help shape the next version of how we deliver: the discovery process, workflow design, adoption model, and playbooks that hold up as we scale. You will be as comfortable running a discovery session with a VP of Operations as you are reviewing an API spec with an engineering team. If you have done this work at a larger company and want more ownership than that environment allowed, this is for you.

What You'll Do

• Run discovery with technical, operational, and executive stakeholders, and lead the room you are in.
• Turn messy reality into future-state blueprints: where AI reshapes a broker workflow, what changes, and what it is worth.
• Own implementations end to end: scoping, build coordination, testing, go-live, training and enablement.
• Own large-scale rollouts across the enterprise: map the organization and sequence onboarding team by team so adoption spreads.
• Drive adoption past go-live, dig into the usage data to find where workflows stall, and identify where Herald should expand next.
• Translate field insights into product direction and drive changes to the internal roadmap.

What You Bring

• 5+ years owning ambiguous, high-stakes outcomes and earning the trust of senior stakeholders. Engagement managers and senior managers from strong consulting firms, or product managers, founders, and forward-deployed or solutions people from high-growth technology companies, all tend to fit.
• A builder's instinct. You want to design and ship the solution, not just diagnose the problem or hand it to someone else.
• Enough technical fluency to shape an integration or AI workflow and hold your own with engineers and executives alike. You will not write production code.
• Executive presence, with a track record of becoming a trusted advisor to decision-makers inside large, complex organizations.
• You can take a half-defined problem, frame it, and drive it to an outcome.
• Experience rolling out AI or automation products is a plus, but real excitement about deploying AI into live workflows matters more.
• Insurance experience helps but is not required. The hard part of this job is learning how commercial brokerage actually works: wholesale workflows, carrier integrations, binding, surplus lines. If you already know that world, you will ramp fast. If you do not, you should be someone who gets up to speed on complex domains quickly and finds that kind of depth interesting.

We Bring

• Competitive compensation packages based on experience
• Company equity
• Hybrid-flexible company focussed in the Northeast (NYC and Boston)
• Relocation stipend (if you want to join us in the Northeast)
• Quarterly in-person meetups (on the company)
• 20 days of PTO (that roll over) + 12 company holidays + 5 sick days
• Quality health, vision, and dental insurance
• Pre-tax commuter benefits to be used towards parking & transit costs for those working hybrid in our offices
• 401K plan
• $500 additional home office stipend (beyond the standard equipment)
• Parental leave for all kinds of parents (including adoption and foster care)
• Agile and motivated team

Additional Information

Diversity, equity, and inclusion are featured prominently in our company's values which you can read about below. Please reach out if you would benefit from any assistance throughout the application or have suggestions about how we can make our process more accessible and inclusive to all people.

One more note: We want to build an incredible team. As a result, we make a point of being open to surprising candidates who are the right person even though their experience does not exactly match up to our job description. Our job descriptions are gestures, not strict criteria. If you think you would be a great addition to our team, but might not fit the criteria perfectly, we still encourage you to apply! We recognize there are many transferable skills and traits that we may not have captured in this description and welcome all interested candidates to apply.

Life at Herald

We're just getting started and building our culture with purpose every day. One of the joys of joining a small company early is that you get to build that culture too. Come join us and help us make Herald an (even more) amazing place to work!

Actions we value

• Build trust
• Create a shared reality
• Get better every day.
• Build a diverse, equitable, and inclusive community.
• (Remember that) we make the rules.