Recruiter
ABOUT OUTMARKET
Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help brokers, MGAs, and carriers extract insights, automate workflows, and move faster by turning unstructured data into action.
We are entering a new phase of growth, and hiring will be one of the most important levers in how we scale. We are looking for a Recruiter who wants real ownership, enjoys building in a fast-moving environment, and is excited to help shape how Outmarket hires as we grow.
ABOUT THE ROLE
We are hiring a Recruiter to own and drive recruiting across the business. You will partner closely with hiring managers and company leadership to run searches, attract exceptional talent, and build a high-quality hiring process.
This is a high-impact role for someone who is energized by ambiguity and wants to do more than simply manage process. You may be kicking off a search for a critical hire, helping a hiring team sharpen what they are looking for, sourcing hard-to-find candidates, or improving how a process runs so we can move faster and hire better. If you like real responsibility, strong partnership with leaders, and creating structure where needed, you will likely thrive in this role.
WHY THIS ROLE
Own recruiting in a way that will have immediate, visible impact on the company’s growth.
Partner directly with hiring managers and leadership on the company’s most important hires.
Help shape the way Outmarket attracts, evaluates, and closes talent as we scale.
Work in a true startup environment where initiative matters and strong operators can build a lot of trust quickly.
Join a high-caliber team built from Meta, IBM, Adobe, Salesforce, DocuSign, and Uber, with real ownership, strong trust, and meaningful equity.
WHAT YOU’LL DO
Own full-cycle recruiting across a range of roles, from kickoff through close.
Partner with hiring managers to define search strategy, hiring criteria, and interview approach.
Build pipelines, source proactively, and engage high-quality candidates for priority roles.
Run efficient, high-touch processes that create a strong experience for candidates and hiring teams.
Keep searches moving by driving alignment, spotting bottlenecks early, and improving the process where needed.
WHAT WE’RE LOOKING FOR
4 to 8+ years of recruiting experience, ideally in high-growth startups, SaaS, or fast-moving technology environments.
A track record of owning full-cycle recruiting and running searches with a high degree of autonomy.
Strong sourcing skills and comfort building pipelines from scratch for hard-to-fill roles.
Strong judgment in candidate assessment and process management.
A builder mindset and comfort stepping into ambiguity without waiting for perfect structure.
Strong communication and stakeholder management skills, with the ability to build trust quickly across all levels of the company.
High attention to detail, strong follow-through, and comfort managing multiple searches at once.
BONUS IF YOU HAVE
Experience recruiting at an early-stage startup.
Experience hiring across both business and technical functions.
Familiarity with interview design, scorecards, and hiring process calibration.
Exposure to vertical SaaS, insurtech, or B2B operating models.
WHAT YOU’LL GET
Competitive compensation and meaningful equity.
Remote-first flexibility, working from anywhere in the United States.
Direct access to leadership and a real voice in how the company hires and grows.
The opportunity to help build the team during a critical stage of growth.
Recruiter
ABOUT OUTMARKET
Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help brokers, MGAs, and carriers extract insights, automate workflows, and move faster by turning unstructured data into action.
We are entering a new phase of growth, and hiring will be one of the most important levers in how we scale. We are looking for a Recruiter who wants real ownership, enjoys building in a fast-moving environment, and is excited to help shape how Outmarket hires as we grow.
ABOUT THE ROLE
We are hiring a Recruiter to own and drive recruiting across the business. You will partner closely with hiring managers and company leadership to run searches, attract exceptional talent, and build a high-quality hiring process.
This is a high-impact role for someone who is energized by ambiguity and wants to do more than simply manage process. You may be kicking off a search for a critical hire, helping a hiring team sharpen what they are looking for, sourcing hard-to-find candidates, or improving how a process runs so we can move faster and hire better. If you like real responsibility, strong partnership with leaders, and creating structure where needed, you will likely thrive in this role.
WHY THIS ROLE
Own recruiting in a way that will have immediate, visible impact on the company’s growth.
Partner directly with hiring managers and leadership on the company’s most important hires.
Help shape the way Outmarket attracts, evaluates, and closes talent as we scale.
Work in a true startup environment where initiative matters and strong operators can build a lot of trust quickly.
Join a high-caliber team built from Meta, IBM, Adobe, Salesforce, DocuSign, and Uber, with real ownership, strong trust, and meaningful equity.
WHAT YOU’LL DO
Own full-cycle recruiting across a range of roles, from kickoff through close.
Partner with hiring managers to define search strategy, hiring criteria, and interview approach.
Build pipelines, source proactively, and engage high-quality candidates for priority roles.
Run efficient, high-touch processes that create a strong experience for candidates and hiring teams.
Keep searches moving by driving alignment, spotting bottlenecks early, and improving the process where needed.
WHAT WE’RE LOOKING FOR
4 to 8+ years of recruiting experience, ideally in high-growth startups, SaaS, or fast-moving technology environments.
A track record of owning full-cycle recruiting and running searches with a high degree of autonomy.
Strong sourcing skills and comfort building pipelines from scratch for hard-to-fill roles.
Strong judgment in candidate assessment and process management.
A builder mindset and comfort stepping into ambiguity without waiting for perfect structure.
Strong communication and stakeholder management skills, with the ability to build trust quickly across all levels of the company.
High attention to detail, strong follow-through, and comfort managing multiple searches at once.
BONUS IF YOU HAVE
Experience recruiting at an early-stage startup.
Experience hiring across both business and technical functions.
Familiarity with interview design, scorecards, and hiring process calibration.
Exposure to vertical SaaS, insurtech, or B2B operating models.
WHAT YOU’LL GET
Competitive compensation and meaningful equity.
Remote-first flexibility, working from anywhere in the United States.
Direct access to leadership and a real voice in how the company hires and grows.
The opportunity to help build the team during a critical stage of growth.
Customer Success Manager (Employee Benefits)
ABOUT OUTMARKET
Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help brokers, MGAs, and carriers extract insights, automate workflows, and move faster by turning unstructured data into action.
Employee Benefits is one of our fastest-growing customer segments, and we are looking for a Customer Success Manager with deep domain expertise to help scale it. This person will serve as a strategic partner to customers and an important internal voice as we continue building our product and go-to-market approach in EB.
ABOUT THE ROLE
We are hiring a Customer Success Manager to own the post-sale customer journey for our Employee Benefits segment. You will report to the Head of Customer Success and work closely with the Chief Revenue Officer, partnering with customers from onboarding through renewal and expansion.
This is a high-impact role for someone who understands the Employee Benefits ecosystem and enjoys building in a fast-moving environment. You will work directly with brokers, agency leaders, and account teams to drive adoption, deepen relationships, and help shape how we scale customer success for this part of the business. If you are energized by ownership, close customer partnership, and helping define the playbook as a company grows, you will likely thrive in this role.
WHY THIS ROLE
Join a fast-growing segment with strong customer momentum and meaningful opportunity ahead.
Work closely with the Head of Customer Success and CRO on customer growth, retention, and expansion strategy.
Own the customer experience end to end, from onboarding and activation through renewal and upsell.
Help shape the product roadmap by serving as a direct voice of the customer for the Employee Benefits market.
Join a high-caliber team built from Meta, IBM, Adobe, Salesforce, DocuSign, and Uber, with real ownership, strong trust, and meaningful equity.
WHAT YOU’LL DO
Own onboarding and activation for Employee Benefits agencies and brokers using the Outmarket platform, driving fast time to value and strong adoption.
Build and maintain trusted relationships with EB group leaders, benefits brokers, and account managers across commercial insurance agencies.
Serve as the primary post-sale point of contact for implementation, training, ongoing engagement, retention, and account health.
Identify opportunities for expansion within existing accounts as customers grow their Employee Benefits business.
Translate customer feedback into actionable product insights that help inform roadmap prioritization.
Build and improve scalable onboarding materials, training content, and Customer Success processes that grow with the business.
Technical Program Manager
About Outmarket
Outmarket is building the AI-native platform for the insurance industry — a unified system spanning workflows, policy checking, document generation, analytics, and deep integrations with carrier and agency-management systems. We move fast, ship continuously, and operate across a complex, multi-tenant technical landscape. Headquartered in San Francisco, we’re a team that pairs serious engineering depth with a relentless focus on delivering real value to insurance professionals.
The Role
We’re looking for a Technical Program Manager (TPM) to be the connective tissue across our engineering and product organization. You’ll own the planning, coordination, and delivery of cross-functional programs that touch multiple teams, systems, and stakeholders. This is a high-leverage role for someone who thrives on bringing clarity to complex, interdependent work and who can speak fluently with engineers, product managers, and leadership alike.
You won’t just track tasks — you’ll shape how we plan, surface and resolve risks before they become blockers, and create the operating cadence that lets a fast-growing team move quickly without breaking things.
What You’ll Do
Own end-to-end program execution for major cross-functional initiatives — from kickoff and scoping through launch and retrospective.
Build and maintain program plans that map dependencies across engineering, product, design, and data teams, keeping everyone aligned on scope, milestones, and timelines.
Drive the operating cadence — run planning cycles, standups, reviews, and launch readiness; make meetings sharp, decisions clear, and follow-ups accountable.
Identify, escalate, and resolve risks and blockers early, proactively unblocking teams and re-sequencing work when priorities shift.
Translate between technical and non-technical stakeholders, turning complex engineering realities into crisp updates for leadership and clear context for the teams doing the work.
Improve how we operate — establish lightweight, scalable processes for planning, prioritization, and delivery that reduce friction rather than add it.
Maintain a single source of truth on program status, dependencies, and decisions, so anyone can understand where things stand at a glance.
What We’re Looking For
5+ years in technical program management, engineering program management, or a closely related role at a software/technology company.
A technical foundation — you can read a system design doc, follow architectural trade-off discussions, and engage credibly with engineers. Prior experience as an engineer, or a CS/technical degree, is a strong plus.
Proven track record shipping complex, cross-functional software programs on time, with multiple teams and competing priorities.
Exceptional organizational and communication skills — you write clearly, run a tight meeting, and keep large groups of people aligned.
Comfort with ambiguity and speed — you create structure where there is none and adapt as priorities evolve in a fast-growing startup.
Strong judgment on prioritization and risk — you know what matters most, what can wait, and what could derail a launch.
Experience with modern delivery tooling (e.g., GitHub, Linear/Jira, Notion) and an instinct for using process to enable, not bottleneck, the team.
Nice to Have
Experience in AI/ML, data platforms, or B2B SaaS products.
Familiarity with the insurance, fintech, or enterprise software domains.
Experience standing up program-management practices at an early- or growth-stage company.
Why Outmarket
High impact, high ownership — you’ll directly shape how a fast-moving company plans and ships.
Work on hard, meaningful problems at the intersection of AI and a massive, underserved industry.
A team that values clarity, speed, and craftsmanship in equal measure.
Competitive compensation, meaningful equity, and the chance to help build the operating backbone of a company in hypergrowth.
Outmarket is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive environment for all employees.
Customer Success Manager (Employee Benefits)
ABOUT OUTMARKET
Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help brokers, MGAs, and carriers extract insights, automate workflows, and move faster by turning unstructured data into action.
Employee Benefits is one of our fastest-growing customer segments, and we are looking for a Customer Success Manager with deep domain expertise to help scale it. This person will serve as a strategic partner to customers and an important internal voice as we continue building our product and go-to-market approach in EB.
ABOUT THE ROLE
We are hiring a Customer Success Manager to own the post-sale customer journey for our Employee Benefits segment. You will report to the Head of Customer Success and work closely with the Chief Revenue Officer, partnering with customers from onboarding through renewal and expansion.
This is a high-impact role for someone who understands the Employee Benefits ecosystem and enjoys building in a fast-moving environment. You will work directly with brokers, agency leaders, and account teams to drive adoption, deepen relationships, and help shape how we scale customer success for this part of the business. If you are energized by ownership, close customer partnership, and helping define the playbook as a company grows, you will likely thrive in this role.
WHY THIS ROLE
Join a fast-growing segment with strong customer momentum and meaningful opportunity ahead.
Work closely with the Head of Customer Success and CRO on customer growth, retention, and expansion strategy.
Own the customer experience end to end, from onboarding and activation through renewal and upsell.
Help shape the product roadmap by serving as a direct voice of the customer for the Employee Benefits market.
Join a high-caliber team built from Meta, IBM, Adobe, Salesforce, DocuSign, and Uber, with real ownership, strong trust, and meaningful equity.
WHAT YOU’LL DO
Own onboarding and activation for Employee Benefits agencies and brokers using the Outmarket platform, driving fast time to value and strong adoption.
Build and maintain trusted relationships with EB group leaders, benefits brokers, and account managers across commercial insurance agencies.
Serve as the primary post-sale point of contact for implementation, training, ongoing engagement, retention, and account health.
Identify opportunities for expansion within existing accounts as customers grow their Employee Benefits business.
Translate customer feedback into actionable product insights that help inform roadmap prioritization.
Build and improve scalable onboarding materials, training content, and Customer Success processes that grow with the business.
Technical Program Manager
About Outmarket
Outmarket is building the AI-native platform for the insurance industry — a unified system spanning workflows, policy checking, document generation, analytics, and deep integrations with carrier and agency-management systems. We move fast, ship continuously, and operate across a complex, multi-tenant technical landscape. Headquartered in San Francisco, we’re a team that pairs serious engineering depth with a relentless focus on delivering real value to insurance professionals.
The Role
We’re looking for a Technical Program Manager (TPM) to be the connective tissue across our engineering and product organization. You’ll own the planning, coordination, and delivery of cross-functional programs that touch multiple teams, systems, and stakeholders. This is a high-leverage role for someone who thrives on bringing clarity to complex, interdependent work and who can speak fluently with engineers, product managers, and leadership alike.
You won’t just track tasks — you’ll shape how we plan, surface and resolve risks before they become blockers, and create the operating cadence that lets a fast-growing team move quickly without breaking things.
What You’ll Do
Own end-to-end program execution for major cross-functional initiatives — from kickoff and scoping through launch and retrospective.
Build and maintain program plans that map dependencies across engineering, product, design, and data teams, keeping everyone aligned on scope, milestones, and timelines.
Drive the operating cadence — run planning cycles, standups, reviews, and launch readiness; make meetings sharp, decisions clear, and follow-ups accountable.
Identify, escalate, and resolve risks and blockers early, proactively unblocking teams and re-sequencing work when priorities shift.
Translate between technical and non-technical stakeholders, turning complex engineering realities into crisp updates for leadership and clear context for the teams doing the work.
Improve how we operate — establish lightweight, scalable processes for planning, prioritization, and delivery that reduce friction rather than add it.
Maintain a single source of truth on program status, dependencies, and decisions, so anyone can understand where things stand at a glance.
What We’re Looking For
5+ years in technical program management, engineering program management, or a closely related role at a software/technology company.
A technical foundation — you can read a system design doc, follow architectural trade-off discussions, and engage credibly with engineers. Prior experience as an engineer, or a CS/technical degree, is a strong plus.
Proven track record shipping complex, cross-functional software programs on time, with multiple teams and competing priorities.
Exceptional organizational and communication skills — you write clearly, run a tight meeting, and keep large groups of people aligned.
Comfort with ambiguity and speed — you create structure where there is none and adapt as priorities evolve in a fast-growing startup.
Strong judgment on prioritization and risk — you know what matters most, what can wait, and what could derail a launch.
Experience with modern delivery tooling (e.g., GitHub, Linear/Jira, Notion) and an instinct for using process to enable, not bottleneck, the team.
Nice to Have
Experience in AI/ML, data platforms, or B2B SaaS products.
Familiarity with the insurance, fintech, or enterprise software domains.
Experience standing up program-management practices at an early- or growth-stage company.
Why Outmarket
High impact, high ownership — you’ll directly shape how a fast-moving company plans and ships.
Work on hard, meaningful problems at the intersection of AI and a massive, underserved industry.
A team that values clarity, speed, and craftsmanship in equal measure.
Competitive compensation, meaningful equity, and the chance to help build the operating backbone of a company in hypergrowth.
Outmarket is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive environment for all employees.
Product Manager - Workflows
ABOUT OUTMARKET
Outmarket is redefining how brokers, MGAs, and wholesalers operate by bringing an AI-first approach to insurance workflows. Our platform helps teams automate repetitive work, make better decisions, and scale more effectively across commercial insurance and employee benefits.
We are building products in close partnership with customers and using AI where it creates real leverage, not just novelty.
ABOUT THE ROLE
We are hiring a Product Manager - Workflows to help design and ship product experiences that make complex insurance operations simpler, faster, and more scalable. This role is well suited for someone who can earn customer trust, translate ambiguity into crisp product decisions, and work closely with engineering to deliver practical AI-enabled workflows.
This is not a role for someone who wants to manage tickets from a distance. You will be close to users, product tradeoffs, and the hard parts of turning AI into software people actually trust.
WHY THIS ROLE
Work directly with users and turn real operational pain into product improvements.
Build AI-enabled workflow software with meaningful day-to-day customer impact.
Operate in a high-ownership environment with short feedback loops.
Partner closely with engineering and go-to-market teams to ship useful, polished features.
Help shape how AI is applied in a practical, trusted way within a traditional industry.
WHAT YOU’LL DO
Work closely with users to understand operational pain points and translate them into product decisions.
Serve as a connective partner between go-to-market and engineering teams.
Design scalable workflow experiences that reduce manual effort and improve operational quality.
Partner with engineering to layer intelligence into key workflow steps.
Measure adoption, usage, and business impact, and iterate based on results.
Support pilot deployments, beta releases, and expansion into new lines by translating commercial needs into product priorities.
Make judgment calls in areas where customer need, product quality, and AI behavior all intersect.
WHAT WE’RE LOOKING FOR
5+ years of product management experience, with at least 2 years in B2B SaaS.
Experience working with engineering teams building AI-enabled products.
Comfort discussing how AI outputs are evaluated and how product design can build trust in AI behavior.
Strong use of AI tools in your own work to accelerate research, writing, and synthesis.
Strong written communication and the ability to explain product rationale clearly.
Strong UX instincts and the ability to simplify complex processes.
Comfort speaking with users, understanding operational pain, and designing practical solutions.
The ability to move quickly without getting sloppy.
BONUS IF YOU HAVE
Direct experience working at or closely with a retail broker, wholesaler, or MGA.
Familiarity with commercial P&C lines or Employee Benefits.
Experience building document-processing or workflow automation products.
Comfort with SQL or basic data analysis.
Previous startup experience, especially in a Series A to Series C environment.
WHAT YOU’LL GET
Real ownership of products that insurance teams rely on daily.
Competitive compensation and meaningful equity.
Direct access to users and strong influence on roadmap decisions.
A builder-oriented culture with fast execution and low ego.
Remote-first flexibility with a distributed, high-performing team.
Applied AI Scientist (PhD)
ABOUT OUTMARKET
Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output.
The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us.
WHAT YOU’LL GET
A high-impact role with ownership from day one.
Competitive compensation and meaningful equity.
Direct collaboration with founders and real users.
Remote-first flexibility.
The opportunity to help build an AI-native product from the ground up.
ABOUT THE ROLE
We are hiring an Applied AI Scientist to push the frontier of what is possible with LLMs, NLP, and machine learning in real-world environments. This is not a role for someone who wants to optimize benchmarks in isolation and hand work off to someone else. It is a role for someone who wants to see advanced research become customer-facing product quickly.
You will work closely with founders, product leaders, and engineers to turn advanced AI techniques into systems that operate under real production constraints.
WHY THIS ROLE
Apply cutting-edge AI research to live customer workflows and production systems.
Work directly with founders and a highly experienced technical team.
Build solutions for document intelligence, quote comparison, workflow optimization, and other high-value use cases.
See your work move from research to deployment in weeks, not quarters.
Help define how applied AI creates advantage in a large, underserved market.
WHAT YOU’LL DO
Research and develop LLM-based solutions for NLP, document intelligence, semantic search, and data extraction.
Design and improve prompt strategies, retrieval-augmented generation systems, and fine-tuned models.
Partner with product and engineering teams to bring AI capabilities into customer-facing workflows.
Build evaluation pipelines and benchmarks for accuracy, performance, and robustness.
Stay current on new research and rapidly test promising techniques in practical settings.
Operate as both a scientist and builder, with direct responsibility for whether ideas survive contact with real data.
WHAT WE’RE LOOKING FOR
PhD in Computer Science, Machine Learning, NLP, or a related field.
Strong research background with publications in top-tier AI venues such as NeurIPS, ACL, ICML, or EMNLP.
Hands-on experience with LLMs, transformers, embeddings, or neural information retrieval.
Proficiency in Python and ML tooling such as PyTorch, Hugging Face, and LangChain.
Track record of applying research in practical, production-oriented systems.
Strong technical judgment about what is novel, what is useful, and what is actually ready to ship.
BONUS IF YOU HAVE
Experience with unstructured data such as PDFs, forms, contracts, or portals.
Background in enterprise or B2B AI applications.
Familiarity with insurance, legal, or document-heavy industries.
WHAT YOU’LL GET
A high-impact role on a team that moves quickly and builds with purpose.
Competitive compensation and meaningful equity.
Remote-first flexibility.
Access to real data, real users, and fast feedback cycles.
The opportunity to bring advanced research to life in a major industry.
Forward Deployed AI Engineer
ABOUT OUTMARKET
Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output.
The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us.
WHAT YOU’LL GET
A high-impact role with ownership from day one.
Competitive compensation and meaningful equity.
Direct collaboration with founders and real users.
Remote-first flexibility.
The opportunity to help build an AI-native product from the ground up.
ABOUT THE ROLE
We are hiring a Forward Deployed AI Engineer to work directly with customers (brokers, MGAs, and carriers) to deploy and tailor our AI solutions to their real workflows. You sit at the intersection of engineering and the customer, turning messy real-world requirements into shipped, working systems.
WHY THIS ROLE
Own customer outcomes end to end, from problem to deployed solution.
Work hands-on with real insurance data and source systems.
Be the technical bridge between customers and the core product team.
WHAT YOU’LL DO
Deploy and configure AI-powered workflows for specific customers and source systems.
Integrate with agency management systems and customer data, and resolve real-world data issues.
Build tooling and feed product requirements back into the core platform.
Partner with sales and customer success to ensure customers succeed.
WHAT WE’RE LOOKING FOR
2+ years in software/forward-deployed/solutions engineering.
Strong Python and SQL, and comfort debugging messy integrations.
Customer-facing instincts and excellent communication.
Bias to action in ambiguous, fast-moving situations.
BONUS IF YOU HAVE
Insurance, fintech, or other regulated-data domain experience.
Experience with LLM-based systems or document processing.
Senior Account Executive
ABOUT OUTMARKET
Outmarket is building the intelligence layer for commercial insurance. Our AI-powered platform helps brokers, MGAs, wholesalers, and carriers unlock value from their data and streamline complex distribution workflows. In an industry that has operated the same way for decades, we are bringing modern infrastructure, automation, and intelligence to a market worth more than $1 trillion.
Our co-founders bring rare depth across product, engineering, and go-to-market leadership from Uber, Meta, Ethos, and IBM Watson. We are already partnering with some of the most innovative agencies and MGAs in the industry, and we are scaling quickly.
ABOUT THE ROLE
We are hiring a Senior Account Executive to help define how Outmarket wins in the market. This is a high-ownership role for someone who knows how to sell a new category, create urgency where none exists yet, and guide buyers through complex change.
You will own deals end to end, partner closely with leadership, and help shape the go-to-market motion as the company grows.
WHY THIS ROLE
Sell into a category you are helping create in a traditional industry ready for change.
Work directly with experienced founders and sales leadership who are invested in your success.
Benefit from a strong mix of inbound momentum, referrals, investor introductions, and deep industry relationships.
Help shape messaging, market strategy, and the sales motion while building your own path for growth.
Earn meaningful equity and uncapped commission in a fast-growing company.
WHAT YOU’LL DO
Own the full sales cycle, including discovery, business case development, negotiation, and close.
Lead complex deals ranging from $25K to $500K ACV, with room to grow beyond that.
Lead with insight: teach buyers something meaningful about their distribution performance before you ever pitch a product
Win new logos as the primary motion, and expand relationships as customers see results
Represent Outmarket credibly with executive buyers at industry events and through association partnerships.
Feed market intelligence back into product, messaging, and leadership decisions.
WHAT WE’RE LOOKING FOR
The most important thing: you know how to sell something new. Our buyers didn't wake up this morning with budget allocated for what we build. You'll need to create the conviction, build the business case, and drive urgency around change in a traditional industry. Beyond that:
Proven track record of meeting or exceeding quota, with clear evidence of performance.
Experience selling disruptive products or emerging categories where you had to create demand, not just respond to it.
Ability to run multiple complex opportunities in parallel with rigor and velocity.
Strong communication and storytelling skills, with a focus on business outcomes over features.
Comfort operating in a fast-moving, early-stage environment where you build process rather than wait for it.
High ownership, strong judgment, and the ability to earn trust quickly with buyers and teammates.
BONUS IF YOU HAVE
Background in insurance, insurtech, or adjacent regulated industries such as fintech, healthtech, or regtech.
Familiarity with carriers, MGAs, brokers, wholesalers, or the commercial insurance distribution chain.
Experience at a Seed, Series A, or Series B company where you helped shape go-to-market from an early stage.
WHAT YOU’LL GET
Competitive salary and uncapped commission.
Meaningful equity in a fast-growing company.
Full health, dental, and vision benefits.
Remote-first flexibility.
Direct access to founders, leadership, and executive buyers from day one.
The full posting opens here — pay, setting and the full description, without leaving the list.