Harper

The Problem 36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We're adding ~1,000 customers per month. We've grown 100x since last year. We're looking to do even more this year—and that's why we're hiring. Once a customer pays, you're the reason the deal actually closes. The Thesis Getting a business insured is only the beginning. After that comes COIs, endorsements, billing questions, renewals, claims—the ongoing reality of being a policyholder. Most brokerages handle this with slow emails and voicemail tag. We handle it with AI and a small, sharp team that actually knows insurance. Every issue you resolve and every interaction you document teaches our AI what to handle next. You're not just serving customers—you're building the system that makes service scale without scaling headcount. The people who learn this operation inside out become the backbone of the company as we grow 20x, 50x, 100x. The Role You own sales operations—the critical last mile of every customer transaction. Once a customer pays, you guarantee that all documents, requirements, and deliverables are in place and the order is fully completed. You're Harper's face in the final stage of the process, pushing every deal through the finish line. We can't score without this team. No two customers behave the same. Every day brings different requirements and different challenges. You capture context quickly, figure out the optimal way to solve each problem, and close it out. You'll work alongside Sales, Engineering, and our AI systems daily. Everything you do feeds back into the product. What You'll Do Own the customer relationship through fulfillment — From payment to certificate delivery, you're Harper's face in the final stage; guarantee every order is completed with all documents and requirements in place Own resolution end-to-end — Don't just take the message; follow up with carriers, track status, close the loop with the customer Know the product — Understand policy types, coverage basics, and carrier processes well enough to answer real questions confidently Feed the AI system — Your work trains the models and algorithms that will automate the manual parts of this process; you're the human component essential for building automation while establishing trust and customer loyalty over time Flag what's broken — Surface recurring issues, edge cases, and friction points so they get fixed upstream by Product and Engineering Keep customers loyal — Every interaction is a chance to reinforce that Harper is different; professional, fast, and actually helpful You Might Be a Fit If… You've worked in sales, operations, or a similar high-volume customer-facing role You're comfortable navigating multiple systems while on a call You take ownership of problems—you don't pass them along and forget about them You're detail-oriented and accurate even when you're moving fast You're excited about AI tools and want to work at a company building the future of the industry You have a product mindset—you want to work closely with the engineering team to shape what AI systems look like You want to grow into operations leadership, product, or deeper roles as the company scales Requirements Prior experience in sales, customer-facing, or operational roles Strong communication skills—clear, professional, and patient Ability to multitask: talk, type, and navigate systems simultaneously Comfort with technology and willingness to learn new tools quickly Based in San Francisco or willing to relocate Nice to Have Insurance industry expe

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. Your operational partner in crime. An extension of the CEO across the entire organization. The Thesis Harper is a deeply founder-led, operationally intense company. The CEO is the connective tissue between sales, ops, growth, and engineering—in the details on submissions, strategy, partnerships, and how we build our AI systems. That intensity is a feature, not a bug. It’s how we scaled 100x in a year. But as we grow, one person can’t be everywhere at once. The Chief of Staff operates the way the CEO does—fast, direct, in the details—and extends his reach across the organization. You’re the person he thinks out loud with, the person who can walk into any room at Harper and drive things forward with the same intensity and context he would. This is an 18–24 month tour of duty. If you crush it, the natural next step is a functional leadership role inside Harper—Head of Ops, Head of Strategy, GM of a new vertical. We promote from within and path people toward P&L ownership. The Role This is not a program management role. This is not an EA role. This is a high-autonomy, high-ambiguity operating role for someone who wants to build a generational company from the inside. You will sit at the center of Harper’s most important constraint at any given moment (people, throughput, quality, speed, execution). Your job is to turn chaos into an operating system—without slowing the company down. What You’ll Do Be an extension of the CEO across the org — Walk into any function (sales, ops, engineering, growth) and drive alignment, remove roadblocks, and push things forward with the same context and urgency Build our operating system from scratch — Leadership meetings, OKR tracking, quarterly planning. None of this exists yet. You create the rhythms that let a 25-person company operate like a 100-person one Own board materials, investor updates, and cap table management end-to-end Drive the highest-priority cross-functional initiative at any given time — M&A (target ID, diligence, integration), new vertical expansion, or standing up operational playbooks as we scale Turn tribal knowledge into systems — A lot of how Harper operates lives in people’s heads. You map it, document it, and build the processes that let us scale without losing what makes us great Plug functional gaps — We’re building the exec team in real time. Until every seat is filled, you step into whatever leadership role the company needs Fix things that are broken before anyone notices they’re broken What this actually means at Harper (real examples): Install an execution cadence that forces clarity: top 3 priorities, owners, deadlines, weekly scoreboards Build repeatable runbooks for messy operational workflows, then push them into automation (human <> AI handoffs) Make sure high-stakes operational surfaces don’t degrade quietly (submission quality, underwriting throughput, quoting speed, customer response time) Increase CEO leverage: fewer “CEO has to touch it” loops, more “it ships anyway” You Might Be a Fit If… You’re 4–7 years in—IB, PE, MBB, startup BizOps, or you built something yourself You actually understand finance—cap tables, driver-based models, unit economics. Not “familiar with,” fluent You’ve owned outcomes, not just advised on them. You stick around to see the results of what you build You can draft a board memo, r

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. Somewhere in that transition, there’s leverage hiding everywhere—inefficiencies the right engineer could eliminate with the right solution built in the right week. The Thesis Turning judgment into compute isn’t a one-time project. It’s a constant hunt for leverage. New models drop monthly. What was impossible in January is table stakes by June. Someone needs to be on the frontier—figuring out what’s newly possible and applying it before anyone else does. That’s this role. The Role You’re a technical generalist who views engineering as a tool for solving business problems—not the end goal itself. You embed with operations: sales, customer service, underwriting, carrier relations. You see where things break. You identify the 20% of problems that cause 80% of friction. Then you build the solution. Prototype Monday, ship Tuesday, measure Wednesday. If it works, push to production. If not, try something else. What You’ll Do Find leverage — Sit with teams, discover what nobody’s automated because nobody knew it could be Build solutions fast — AI agents, automations, internal tools—prototype in days, ship in weeks Stay on the frontier — New model drops? You’re testing it that day Prove impact — Set up metrics, track results, show what worked Communicate what you learn — Present to the company; shape the roadmap You Might Be a Fit If… You get energy from business impact, not code elegance You’re a technical generalist (Python, TypeScript, SQL—you learn new tools in days) You write code with AI (Cursor, Claude Code) and can manage multiple coding sessions You can present to non-technical people and explain why conversion dropped You think in business terms: “we increased conversion by 15%,” not “we shipped the feature” You’re 2-5 years into your career Requirements 2-5 years software engineering experience Proficiency in Python, TypeScript, or similar Experience building and shipping internal tools or automations Ability to work autonomously and move fast Based in San Francisco or willing to relocate Nice to Have Experience with LLMs, AI agents, or voice AI Background in operations, sales tech, or workflow automation Prior startup experience Compensation Salary: $140,000–$200,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace If in SF: Super Day on-site If outside SF: Technical phone screen, then on-site To Apply If you want autonomy, impact, and the chance to build AI capabilities against business problems you discover yourself—send your resume and tell us about something you built that had measurable business impact.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll be the closer who proves it works—and the architect who makes it scale. The Thesis This is a founding role. You’ll close deals from day one, but you’ll also build the sales infrastructure that lets us scale without adding headcount. Every workflow you design, every AI-assisted system you create, every playbook you write becomes company DNA. Winning in 6-12 months means revenue growth AND a sales engine that runs itself. The Role You’re a hardcore closer who could sell sunscreen in a snowstorm. But you’re also obsessed with using AI tools to close faster and providing the feedback that makes those tools better. You work directly with founders. No committee. No approval chain. You close it, you build it, you own the outcome. You don’t need insurance expertise on day one—we’ll teach you. What You’ll Do Close deals — Master the playbook by week one, improve it by week two; measure success by revenue generated Use AI tools to close faster — Leverage AI to eliminate friction and increase your velocity Provide feedback that improves the tools — Your insights from live calls make our AI smarter Expand into new lines — Close across new insurance products as we scale You Might Be a Fit If… You’re a closer first—proven track record of closing at high velocity You’re obsessed with systems—you figure out how to 10x team effectiveness You leverage AI strategically (crafting pitches, building automated qualification workflows) You think in first principles and build complex systems in one-third the normal time Ex-founders are a plus Requirements Proven track record in high-velocity sales Experience turning sales intuition into scalable systems Comfort with environments where everything changes daily Ability to leverage AI tools for sales automation Based in San Francisco or willing to relocate Willingness to obtain required insurance licenses (we’ll pay for training and licensing) Nice to Have Ex-founder experience building and scaling sales teams Background in insurance, fintech, or regulated industries Track record of designing sales playbooks that scale Insurance license (we’ll pay for training and licensing for the right candidate) Compensation Salary: $100,000–$200,000 + performance bonuses & commission Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process Founder screen — Initial fit and alignment Lead screen — Skills and culture fit Super day — See how you operate in real time To Apply If you’re excited about building something massive and owning a meaningful piece of it—send your resume and tell us about the last sales system you built or broke.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll be Harper’s first Product Manager, building the connective tissue between engineering and the business. The Thesis We need a technical PM who really understands what we’re building—how AI agents work, how context engineering shapes outcomes, how our systems make decisions. You’ll be the translator between engineering and business, and the gelling function that keeps sales, service, and engineering building toward the same outcomes. This is a rare path to Head of Product. The Role Founding role. You’ll bring owner-style ownership of the end-to-end product lifecycle—the right mix of product management, product marketing, and strategic vision. You work directly with founders to set strategy, manage technical development, and own success from concept to launch. You won’t own a single product—you’ll own a product area. Deeply live and breathe a customer persona. Drive a business outcome. What You’ll Do Use AI to prototype fast — Spin up prototypes with Claude Code, Cursor, Lovable; show, not tell Bridge engineering and business — Understand data systems deeply enough to explain what’s possible Be the gelling function — Break down walls between teams; create shared context Own a product area end-to-end — Strategy, roadmap, execution, outcomes Drive business outcomes — North star is revenue and customers, not features shipped Talk to customers every day — Literally You Might Be a Fit If… You prototype with AI tools (Claude Code, Cursor, Lovable)—you build before the meeting You’re a natural translator between technical architecture and business outcomes You understand data systems deeply (pipelines, AI/ML, APIs, integrations) You’re a connector who fixes when teams talk past each other You’ve shipped B2B products from 0→1 and you’re customer-obsessed You’re not a project manager—you decide, you have strong opinions, you execute Requirements 3-6 years in product management (B2B SaaS or AI-native preferred) Technical depth in AI agent architecture, context engineering, LLM-based systems Proficiency using AI tools to rapidly prototype Success owning a product from concept through launch Track record bridging engineering and business teams Based in San Francisco or willing to relocate Nice to Have Insurance, fintech, or regulated industry experience Background in AI/ML products, voice AI, or workflow automation Prior startup experience (Series A/B) Experience building product functions from scratch Compensation Salary: $135,000–$185,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process Founder screen — Initial fit and alignment Product case study — Show us how you’d approach a real problem (~1 day turnaround) On-site day — Meet the team, walk through your case study, see the product To Apply If you’ve built products from zero and can bridge engineering and business like a native speaker of both—send your resume and tell us about a time you connected teams that weren’t connecting.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. Founder training disguised as a job. 12 months here equals 5 years anywhere else. The Thesis To build AI that amplifies human judgment, you first have to understand the work at a molecular level—the exceptions, the precedents, the decision traces that currently live in people’s heads. You’ll spend 6-18 months embedded in Harper’s operations, then help design the systems that make everyone more effective. The Role This is not an analyst role. This is founder training. You’ll do the work—sales calls, processing applications, customer service—and document every edge case. Then you’ll create templates that turn tribal knowledge into structured data. Everyone at Harper has agency to build. Use Claude Code, Lovable, Cursor. Get your hands dirty. Three tracks: Business Development, Sales, or Customer Service. What You’ll Do Learn by doing — Take sales calls, process applications, handle customer service, work with underwriters Build systems — Document every process, decision, and edge case you encounter Create templates — Turn tribal knowledge into structured data and workflows that scale Work with engineering — Build automation on top of what you’ve learned You Might Be a Fit If… You’re early in your career but already exceptional (recent grad or 0-2 years) You have founder DNA—always building things, never waiting for permission You’re willing to go deep before going wide You recognize patterns others miss and immediately think about how to fix them You want to compress 5 years of learning into 12 months Requirements Recent grad from a top program, or 0-2 years with standout experience High agency and ownership mentality Strong communication skills Based in San Francisco or willing to relocate Nice to Have Started something (company, project, community) Technical background or comfort with AI tools Experience in customer-facing roles Compensation Salary: $125,000–$170,000 (depending on experience) + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace Case study / problem-solving exercise — Show us how you think On-site day — Meet the team, see the operation To Apply This is a launching pad—into leadership within Harper, or to found your own AI company someday. If you want to compress years of learning into months—send your resume and a few sentences on why Harper.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. To grow that fast, we need to understand—with precision—what’s working, what’s not, and why. The Thesis The line between “analytics” and “product” barely exists here. Your models will directly power how our agents prioritize leads, time outreach, and personalize conversations. You’ll build the intelligence that tells us how well it’s working—and ship code that directly moves revenue. The Role You’ll own the metrics, analytics, and experimentation infrastructure that powers growth. This isn’t “build dashboards and wait for questions.” You’ll define the KPIs that matter, instrument systems to track them, and ship code that directly moves revenue. You work across paid acquisition channels—Google Ads, Meta, TikTok—combining it with product analytics and using AI to surface insights that would take others weeks to find. What You’ll Do Build metrics and KPI infrastructure — Define, instrument, and own the metrics that matter in real time Own LTV/CAC systems — Track unit economics across verticals, channels, and cohorts Build paid channel analytics — Connect ad spend to actual revenue, not vanity metrics Create attribution that works — Multi-touch attribution across voice, email, web, and referral Use AI for insight generation — Pattern detection, anomaly detection, automated analysis Ship experimentation infrastructure — A/B testing with statistical rigor You Might Be a Fit If… You ship code—production code, not just notebooks (Python, SQL) You’ve defined KPIs, built instrumentation, and been accountable for moving them You’ve worked with paid acquisition data (Google Ads, Meta, TikTok) You use AI to accelerate analysis (PostHog or similar) You’ve built GTM systems: lead scoring, attribution, LTV/CAC analysis You think in experiments and know correlation vs. causation You’re 2-5 years into your career Requirements 2-5 years experience in analytics engineering or growth engineering Strong Python and SQL skills Experience with paid acquisition data and funnel analytics Ability to ship production code, not just analysis Experience with A/B testing and experimentation Based in San Francisco or willing to relocate Nice to Have Experience with PostHog, Amplitude, or similar product analytics Background in lead scoring or attribution modeling Prior startup or high-growth company experience Compensation Salary: $130,000–$190,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace Technical conversation — Walk us through analysis you’ve done On-site — Meet the team, see the data To Apply Data talks. Narratives walk. If you prove things instead of just believing them—send your resume and an example of analysis that drove a business decision.

The Problem 36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We're adding ~1,000 customers per month. We've grown 100x since last year. We're looking to do even more this year—and that's why we're hiring. We're taking 5,000 customers to 100,000+ this year, and 1M+ from there. This is extreme hypergrowth—and Customer Experience is where it all gets real. The Thesis You'll open the ticketing system on day one. You'll work real customer issues—COIs, billing disputes, claims questions—to learn the operation from the inside. You've done this before. It's how you've always ramped, and you wouldn't have it any other way. We're not a brokerage that uses AI—we're computational insurance distribution. We've already built the AI infrastructure: our own operating system, our own AI agent, our own internal tooling. Your job isn't to replace any of that with off-the-shelf software. It's to shape it—to define what the human layer should be and work directly with engineers to build the systems that let CX scale non-linearly. This isn't a call center leadership role. It's an operator + builder role where the question isn't "how do we respond faster?"—it's "why are we responding at all?" The Role You own the full service lifecycle and outcomes: COIs, endorsements, renewals, claims coordination (triage, carrier comms, customer guidance), billing escalations, carrier follow-ups, quality, and escalation management. You own the product roadmap for CX tooling. You spec it, you prioritize it, you validate it in production with real metrics and real customer feedback. You work directly with engineers as a thought partner—not a requestor who submits tickets and waits. When there's a tooling gap, your instinct is to figure out what you can build with what exists, not to evaluate vendors. You'll inherit a small, experienced team of insurance industry veterans. You're not starting from zero—but you're building the scalable version. There is no large support structure waiting for you. No dedicated CRM team, no project managers, no integration specialists. You'll operate with what's here and build from it. Reports directly to CEO. This is a small team, high-intensity, high-ambiguity environment. The CEO is in the weeds daily. Everyone operates well beyond their job description. If that sounds like where you do your best work, keep reading. What You'll Do Get in the queue — Work real tickets and escalations from day one to learn the customer, the product, and the operation from the inside out Ship quick wins — Immediately reduce repeat contacts and rework while building the long-term model Own end-to-end customer experience — COIs, endorsements, renewals, claims coordination, billing escalations, carrier follow-ups, quality, and trust Own the CX product roadmap — Spec, build, and validate CX tooling with engineering: customer portal, self-serve flows, routing/triage, automation guardrails. You are the product thinker for this domain. Build scalable systems — Map workflows into AI → self-serve → human → escalation; instrument everything Establish the defect loop — Weekly cadence with Product/Eng so recurring issues get fixed upstream, not patched with more headcount You Might Be a Fit If… Your first move in a new role is to open the ticketing system and start working real issues You've been in a CX/Ops role during hypergrowth—you know what breaks at 10x, 50x, 100x You've been at a company between Series B and IPO and lived through what breaks at each stage You've built systems that survive extreme scale, not just hired pro

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll build the AI systems that operate Harper—not features, the actual intelligence that runs the company. The Thesis This is full-stack in the truest sense: the interface a customer sees, the backend that powers their entire journey—application, business data, history, ongoing service—and the AI layer that makes decisions. Your code ships to production and generates revenue the same week you write it. The Role You’ll build AI agents, workflow orchestration, and voice AI that actually works. Not demos—real systems serving real users at scale. You work directly with founders. No committee. No approval chain. You build it, you ship it, you own the outcome. What You’ll Do Build AI agents that run the business — Lead qualification, customer service, underwriter follow-up—all without human intervention Create workflow orchestration — Document retrieval, carrier API calls, compliance checks, human review—coordinated across thousands of concurrent transactions Ship voice AI that actually works — Handle skeptical business owners asking “wait, what does that actually cover?” Build systems that compound — Every decision gets traced; every outcome feeds back; the AI gets smarter with each interaction You Might Be a Fit If… You write code with AI (Cursor, Claude Code, Windsurf) and can manage multiple coding sessions You’ve shipped AI to production—real systems serving real users You’re full-stack by instinct (frontend, backend, infrastructure) You ship fast and iterate—meaningful features in days that others take months on You’re 1-4 years into your career Requirements 1-4 years software engineering experience Experience with LLM applications, agent pipelines, or AI systems in production Proficiency in Python, TypeScript, or similar Ability to work across the stack Based in San Francisco or willing to relocate Nice to Have Voice AI or real-time systems experience RAG systems or workflow automation background Prior startup experience Compensation Salary: $140,000–$200,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace If in SF: Super Day on-site If outside SF: Technical phone screen, then on-site To Apply If you want to build something that’s never existed, ship code that runs a real business, and work with people who show up with the same intensity every day—send your resume and a link to something you’ve built.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. To do that, we need to assemble one of the highest-caliber teams in the industry. That’s where you come in. The Thesis You’ll be Harper’s first dedicated recruiting hire—building the talent function from the ground up while closing candidates yourself. You’ll build the systems that let Harper scale from 30 to 100+ without creating chaos—and you’ll think about what we need 24 months from now, not just today’s reqs. In 6-12 months, you’ll have built a repeatable recruiting machine that can handle 10x growth AND filled critical roles yourself. This is execution AND strategy. The Role This isn’t a coordination role. You’re sourcing, selling, and closing exceptional people across engineering, sales, and GTM. Technical recruiting background preferred—you understand tech stacks, know which competitors to pull from, and have a developed mind map of the landscape. You work directly with founders. No committee. No approval chain. You source it, you sell it, you close it. What You’ll Do Close candidates yourself — Sourcing, screening, selling, closing engineering and GTM roles Build recruiting infrastructure for 10x scale — Repeatable sourcing strategies, structured interviews, calibrated scorecards that don’t break when we triple headcount Own technical recruiting — Understand the tech stack; evaluate whether an engineer is actually good Expand into GTM and operations — Once technical recruiting runs, build pipelines for sales/marketing/ops Partner with founders on hiring strategy — Push back when job specs don’t make sense; think 24 months ahead Build and lead a team — Hire and manage recruiters as we scale; set the bar for performance and velocity You Might Be a Fit If… You’re a closer with a technical background (years recruiting engineers) You’ve scaled recruiting through rapid growth phases—not just early-stage setup, but the ebbs and flows of Series A through C You’ve built systems, not just filled roles—and you think about what breaks at 10x You have tenure and depth (2-3 year in-house stints where you saw real scale) You move at founder speed—close great candidates this week, not next month You can sell a trading floor culture (intense, loud, collaborative) You’re ready to own the function and build a team under you Requirements 6-10 years in recruiting, with experience scaling through rapid growth (Series A-C) 2+ years managing recruiting teams of 3+ people Technical recruiting background strongly preferred Experience building recruiting processes and systems that survive 10x growth Ability to source, sell, and close directly—not just manage Deep understanding of technical roles and talent landscape Based in San Francisco or willing to relocate Nice to Have Experience at companies that scaled from 30 to 200+ (not just repeated Series A stints) Background recruiting for AI-native or technical sales organizations Employer brand and recruiting content experience Experience building recruiting teams from scratch Compensation Salary: $185,000–$250,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process People screen — Initial fit and alignment Founder screen — Skills and culture fit Super day — See how you operate in real time To

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll be one of the most senior engineers at Harper. That means you own systems end-to-end. The Thesis The difference between MTS and Senior MTS: you own outcomes, not tasks. You look at a business problem—“we need to 10x our quoting capacity”—and figure out what to build, build it, and make sure it works. You architect systems AND implement them. You mentor by building alongside people, not by reviewing PRs from a distance. The Role This isn’t a “tech lead who attends meetings” role. You make architectural decisions that stick, and ship code that directly generates revenue. No waiting for consensus—we don’t have time for consensus. What You’ll Do Own core AI infrastructure — LLM orchestration, prompt management, retrieval systems, structured output parsing Design agent architecture — Define abstractions that let us ship new agents in days Build evaluation that works — Systems that measure whether agents are getting better at closing deals Architect decision trace capture — Make every AI judgment traceable Own platform scale — Thousands of concurrent conversations, sub-second response times You Might Be a Fit If… You’ve owned production systems (not contributed to—owned; you got paged when it broke) You architect AND implement—the best architecture comes from people who live with what they build You’ve built AI systems in production (LLM applications, agent frameworks, RAG, voice AI) You write code with AI (Cursor, Claude Code) and manage multiple sessions You’re 3-6 years into your career Requirements 3-6 years software engineering experience Production experience with LLM applications and AI systems Strong architectural skills with hands-on implementation Track record of owning systems end-to-end Based in San Francisco or willing to relocate Nice to Have Voice AI or real-time systems experience Experience building agent frameworks or evaluation systems Prior startup experience Compensation Salary: $160,000–$230,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace If in SF: Super Day on-site If outside SF: Technical phone screen, then on-site To Apply If you want to own systems that run a real business and work with founders who will actually listen to you—send your resume and tell us about a system you’ve owned.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Voice is the lifeblood of insurance. Businesses call brokers. Brokers call underwriters. The industry runs on phone conversations—millions of calls per day, most of them repetitive, most of them waiting on hold. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. Voice is how trust gets built. Voice is how deals get closed. Voice is where the industry lives. The Thesis Voice is the hardest part to make computational. Getting voice right is what separates AI demos from AI that operates. Companies like Giga (DoorDash) and HappyRobot (DHL, Ryder) are proving that voice AI can run core operations at enterprise scale. We’re building the same for insurance. The Role You’ll own our entire voice AI infrastructure—architecture, implementation, scaling, continuous improvement. Voice isn’t a feature at Harper. It’s a core system that powers sales, operations, and customer service. Today we have working voice agents. But we’re at 1% of where we need to be. We need to scale from hundreds of calls to thousands. From functional to exceptional. What You’ll Do Build outbound at scale — Lead qualification agents calling thousands of prospects daily Create inbound customer service — 24/7 agents handling policy questions, certificate requests, claims Ship operations and underwriting voice — 20-30 minute insurance applications over the phone Build platform infrastructure — Move to custom infrastructure; sub-700ms latency; 10,000+ concurrent calls Design systems that compound — Every conversation becomes structured decision traces You Might Be a Fit If… You’ve built production voice AI (not demos—significant production volume) You know both fast deployment (VAPI, Retell) and custom infrastructure (Pipecat, LiveKit) You understand telephony (SIP, RTP, WebRTC) You’ve achieved sub-second latency in production You write code with AI (Cursor, Claude Code) You’re 3-6 years into your career Requirements 3-6 years software engineering experience Production voice AI experience at scale Deep knowledge of voice infrastructure and real-time systems Experience with latency optimization Based in San Francisco or willing to relocate Nice to Have Telephony background (SIP/RTP) Experience with specific platforms (VAPI, Retell, Pipecat, LiveKit) Prior startup experience Compensation Salary: $170,000–$275,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process 15-min founder call — Alignment on mission and pace If in SF: Super Day on-site If outside SF: Technical phone screen, then on-site To Apply Voice is the highest-leverage problem in our stack. If that’s the challenge you want—send your resume and links to voice systems you’ve built.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. You’ll build and run the operational backbone that lets Harper scale from thousands to tens of thousands of customers monthly. The Thesis This is hands-on leadership in the truest sense: building infrastructure while running it, making real-time decisions while documenting them, hiring a team while doing the work yourself. Your operational calls directly impact revenue, compliance, and customer experience—often the same day. The Role Not “manage a department”—own the entire operational engine of a company transforming how insurance gets distributed. Long hours, rapid change, incomplete information, high stakes. You work directly with founders. No buffer. You build it, you run it, you own the outcome. What You’ll Do Own end-to-end brokerage operations — Policy administration, renewals, endorsements, certificates, billing, compliance Build operational infrastructure from scratch — SOPs that scale to 10,000+ customers monthly Lead technology and systems integration — Agency management systems, CRMs, carrier portals Own compliance and risk management — Full regulatory compliance across every jurisdiction Build a team that performs under pressure — Hire, train, manage ops staff; lead from the front You Might Be a Fit If… You’ve run brokerage operations at scale (10+ years commercial insurance operations) You know commercial lines products, brokerage workflows, and agency management systems (Epic, Applied TAM, AMS360) You’ve built, not just managed—thrived in chaos, not just tolerated it You solve problems, not defer them (ownership mentality, bias toward action) You want intensity: long hours, high urgency, rapid change You have regulatory and compliance knowledge (CPCU, CIC, CRM, ARM preferred) Requirements 10+ years in commercial insurance operations Full operational ownership experience (not just a piece) Experience in startup, scale-up, or high-growth environment Deep knowledge of brokerage workflows and agency management systems Strong regulatory and compliance knowledge Based in San Francisco or willing to relocate Nice to Have Insurance designations (CPCU, CIC, CRM, ARM) Experience building ops infrastructure from scratch Prior startup experience Compensation Salary: $180,000–$220,000 + performance bonuses & equity Location: San Francisco, in-office Benefits Health, dental, and vision insurance Commuter benefits Team meals and snacks The Process Initial screen — Skills and culture fit 30-min founder call — Alignment on mission and pace On-site Super Day — Meet the team, work through real scenarios Paid work trial — Real work, real stakes, mutual evaluation To Apply If you want to build the operational engine of a company that’s never existed and own outcomes that matter—send your resume and tell us about the hardest operational challenge you’ve solved.

The Problem 36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. We just closed our $36M Series A. We’re at an inflection point where the systems we build now determine whether we scale from $30M in premiums to $300M—and eventually to billions. The Thesis This role is custom-built for someone who can operate as a future founder inside Harper. Someone who thinks holistically about the business, understands the customer deeply, and solves first-principles challenges across product, operations, growth, and automation. This is not a job with a fixed scope. The company is changing fast. What we need is someone who can flex across the business and tackle whatever becomes most urgent. Week to week, it will shift. The work you do will meaningfully shape the company’s trajectory. The Role You’ll work directly with the CEO on the hardest problems in the business—with inclusion in everything substantive. Biz ops, growth, strategic projects, investor materials, M&A diligence, and whatever else becomes urgent. The goal is for you to see every part of this business, deeply. If you perform the way we think you can, this role evolves into whatever makes sense—running a function, becoming a true right-hand, or using what you learn here to go build your own thing. You’ll understand how to build a company, start a company, and run a team. What You’ll Do Tackle the CEO’s hardest problems — Direct access to everything substantive; scope shifts week to week based on what’s most critical Build 0→1 systems — Across underwriting operations, customer experience, and risk evaluation; leverage AI to replace historically manual brokerage workflows Run deep analysis — Customer interactions, underwriting requirements, operational workflows; uncover patterns, improve conversion, increase throughput Bridge engineering, operations, and growth — Translate customer needs and market realities into product requirements and iterative improvements Own mission-critical problems end-to-end — Gather data, map the system, identify constraints, propose solutions, run experiments, drive to completion Manage cross-functional initiatives — Coordinate across engineering, carriers, underwriters, and customers with speed, clarity, and high quality Build the intelligence layer — Dashboards, metrics, and reporting structures that surface truth and drive clarity on throughput and efficiency You Might Be a Fit If… You have raw analytical horsepower and think in systems You have a bias toward action—you move toward execution, not away from it You’re not afraid to engage with complexity; you’re energized by it You care deeply about getting things done with excellence You’re eager to learn and constantly pursuing improvement You’ve worked in high-intensity environments (banking, consulting, PE, high-growth startups) and thrived You want exposure to every part of building a company—and you’re willing to work for it Requirements 2-5 years in high-intensity analytical or operational roles (investment banking, private equity, management consulting, or equivalent startup experience) Exceptional analytical skills—comfortable with complex data, financial modeling, and ambiguous problem sets Strong written and verbal communication Ability to operate autonomously and context-switch rapidly Track record of delivering under pressure with high standards Based in San Francisco or willing to relocate i