About the role
Pathpoint's Business Operations team builds and runs the production systems behind how we quote, bind, and service E&S insurance for 25,000+ agencies nationwide. This role exists to make our customer communications best in class: everything an agent or insured hears from us, across email, campaigns, and telephony, and the AI systems that increasingly draft and drive it. In parallel, you’ll build the automations that keep agents and insureds informed without anyone having to reach out in the first place.
You will take end-to-end ownership of our communications and AI tooling domain: lifecycle and campaign messaging, our shared email operations layer, our telephony and conversation-intelligence surface, and a growing set of production AI agents that draft, triage, and respond to customer communications.
We are looking for someone who thrives on problem-solving and is unfazed by ambiguity. You will own the systems, the processes around them, and the outcomes they produce. That ownership extends past the current infrastructure: we expect you to proactively find problems worth solving, including ones that don't fit neatly inside today's workflows, and to bring teams along as you change how things work.
What you'll own
- The communications platform stack end to end:
- Customer.io: segmentation, Liquid templating, lifecycle and transactional campaigns, and the data pipeline that feeds them.
- Front: email routing, triage, automation, and turning high-volume inbound into signal.
- Dialpad: telephony administration, insight generation, and making our call data as useful as our written channels.
- Production AI systems in this domain: extending and operating our existing AI email agents, shipping in-flight builds like our AI help center chat, and developing new agent workflows across the operations and go-to-market teams.
- Quality and rollout for customer-facing communications: evaluation approaches, guardrails, staged releases, and the judgment to know when an AI system is ready for production and when it isn't.
What you'll work across
You'll operate in a business operations team, which means domain ownership comes with range. You won't be the deepest person in these on day one, but you'll be expected to work in them independently:
- Salesforce, as a capable administrator: objects, flows, reports, and how changes ripple through an org that runs the business.
- SQL against a production warehouse for analysis, campaign targeting, and measuring whether what you shipped actually worked.
- The n8n automation layer where workflows that integrate Salesforce, our communications platforms, and LLM APIs live.
- The connective tissue of a modern ops stack: APIs, webhooks, data syncs, and reading unfamiliar systems quickly.
What we look for
- 3-6 years in marketing operations, revenue operations, business operations, or a similar systems-heavy role. We care more about what you've shipped than how long you've been shipping. If your experience is unusually deep for its length, we want to hear from you.
- Hands-on experience building with AI in production, not just using it. You've shipped LLM-powered workflows or agents that real users depend on, you've dealt with prompt regressions, evaluation, and failure modes, and you have opinions about what makes AI systems reliable versus demo-ware.
- Deep platform skill in at least one communications system (Customer.io, Braze, Iterable, or similar), including templating logic and data integration, not just campaign building.
- Working SQL and demonstrated comfort administering Salesforce or an equivalent CRM at the object and automation level.
- Strong communication judgment. This role will own domains where language is going out under our name, written or spoken through our systems, and you can tell the difference between a message that's fine and one that's right.
- An owner's disposition. You debug your own work, you fix root causes rather than filing tickets, and when something breaks near your domain, your first move is to pick it up, not to ask whose it is.
Nice to have
- n8n, Zapier, or similar workflow-automation depth
- Insurance or fintech operations exposure
- Experience being the sole or founding owner of a system surface
- Experience building system integrations
- Prior roles in Sales Operations, Marketing Operations, or Revenue Operations
- Insurance coverage fit for an insurance company – with some plans at no cost to you
- Competitive compensation, equity, and total rewards
- 401(k) with an annual company match
- 20-days of PTO (increased to 25-days after 2-years)
- Professional development opportunities
- Remote-first working environment with investments in in-person collaboration
- Annual $500 home office stipend
- Monthly $75 internet stipend
- Generous paid parental leave
- An early stage insurance company offering unique opportunities for growth
Pathpoint's Values:
Hard Problems Drive Us: We believe the insurance industry hasn’t kept up with changing times and fixing that is a hard problem worth solving.
We Start with Why: Seek to understand what customers care about. Use data to challenge assumptions and figure out the problem.
We Take Ownership and Accountability: We think people are their happiest when they have high ownership and accountability over the problems confronting them and are empowered to move decisively to work on them.
We Work Together: Nothing happens without the individual efforts of our team members, but effective teamwork is how we build and maintain customer value.
We Move Forward: We value the ability to persist through adversity to achieve goals and believe speed plays an important role.
Notes:
We are unable to provide visa sponsorship for this position at this time. By applying to this job, you confirm that you are eligible to work in the U.S. without requiring visa sponsorship now or in the future. Thank you for your understanding.
Pathpoint is an equal opportunity employer that values diversity, inclusion, and belonging. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
Skills Required
- 3-6 years of experience in marketing operations, revenue operations, business operations, or a similar systems-heavy role
- Hands-on experience building and operating AI-powered workflows or agents in production
- Experience handling LLM prompt regressions, evaluation, reliability, and failure modes
- Deep platform expertise in at least one communications system such as Customer.io, Braze, Iterable, or similar
- Experience with templating logic and data integration for communications platforms
- Working knowledge of SQL
- Experience administering Salesforce or an equivalent CRM at the object and automation level
- Strong written and spoken communication judgment
- Experience with n8n, Zapier, or similar workflow automation tools
- Insurance or fintech operations experience
- Experience being the sole or founding owner of a system surface
- Experience building system integrations
- Prior Sales Operations, Marketing Operations, or Revenue Operations experience
What We Do
Placing small E&S risks shouldn’t be hard. Pathpoint was built to make it faster and easier for retail agents to get great E&S coverage options. Quote and bind coverage for your small business clients online with one streamlined submission. Receive multiple bindable quotes for your clients in minutes, not days.
