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Deployment Strategist

New York, NY

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: 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’re a team of insurtech veterans with experience at At-Bay, Kin,  and Insurify. We’ve raised our Series A funding from top-tier VCs (Lightspeed, Brewer Lane,  Afore, Underscore) along with a panel of insurtech founders (At-Bay, Marble), insurance executives (CRC), and early employees of other successful API infrastructure companies (Plaid, Alloy).

The role

You bring AI into commercial insurance brokerages and own that transformation end to end , 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 hold a high bar here on purpose. We also know strong people come from unexpected places, so if you read this and recognize yourself even when your background does not match line for line, we want to hear from you. If you would benefit from any accommodation during the process, tell us.

What 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)
  • 🏃‍♀️ An agile and motivated team

Full compensation packages are determined based on candidate experience. Please note that some roles may include variable compensation (such as commission, bonuses, and/or equity) that are not outlined here. This range is depicting base pay only. Any variable compensation will be discussed throughout the hiring process.

New York Pay Range

$150,000 - $170,000 USD

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 doesn't 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

There are many actions that we hope for and even demand from members of our team: communicating honestly, working hard, behaving with integrity. These are expectations. But we value these five actions above and beyond the level of "baseline expectation." We believe that if we excel at these, our business will thrive. We’re betting the company on it.

Build trust 

We always lead with empathy. We publicly own and learn from our mistakes just as we are confident and transparent in explaining our decisions. And we help get the work done because we recognize that no job is too small.

Create a shared reality

We each articulate the facts, assumptions, questions, and fears we hold about our business. We listen to and learn from others. We create a shared set of information before making decisions.

Get better every day.

We constantly seek ways to improve ourselves. We provide each other candid feedback coupled with support to elevate those around us. We refine how we work together to become more effective as a team.

Build a diverse, equitable, and inclusive community.

We thrive when our team has a variety of lived experiences, values each other for their unique perspectives, and shares equitably in our mutual success. We invest in building an inclusive community for people who are oppressed because of their race, ethnicity, age, religion, gender expression, sexual orientation, physical ability, or socio-economic class.

(Remember that) we make the rules.

We once created the ways we work and therefore can change them. We do not default to momentum. We challenge ourselves to deconstruct the status quo and create a better future.

 

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