Deployment Strategist

About Us

Herald is transforming how commercial insurance gets sold. We combine modern API infrastructure with industry‑specific AI that can read emails, extract data, generate quotes, and guide brokers through submission workflows end‑to‑end. The result is faster placement, cleaner operations, and meaningful revenue growth. The market is huge, the need is obvious, and the product we’re building doesn’t exist yet. If you want to help shape the operating system for modern insurance, we’d love to work with you.

We are a team of insurtech veterans with experience at At‑Bay, Kin, and Insurify. We have raised our SeriesA funding from top‑tier VCs and panels of insurtech founders and insurance executives.

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.

• 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.

• 5 years owning ambiguous, high‑stakes outcomes and earning the trust of senior stakeholders.
• 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.

• 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) with 12 company holidays and 5 sick days.
• Quality health, vision, and dental insurance.
• Pre‑tax commuter benefits to be used towards parking and 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.

New York: $150,000 – $170,000 USD.