Sales Executive-Property & Casualty Insurance Tech
These are Questions I ask the CEO to get a better understanding of the Opportunity, the Culture and the Solution. The actual job description is at the end of the Q&A.
1) My candidates will be recruited candidates that are happy at the current job and making their numbers, so we have to be able to show them there is a better opportunity at The Company. What is the sizzle around The Company? What does your Solution do for the client?
● The Company is unlocking the promise of AI for P&C Carriers. By leveraging technology, The Company has proven results showing that we enable our customers to:
○ Win more business through faster broker responsiveness and cycle-time reduction
○ Improve risk selection, consistency, and downstream decisioning
○ Get in front of the retiring workforce problem by automating manual tasks and stabilize operations without hiring
● We have 7 of the top 15 commercial carriers as clients - all in production - (with a total of 25 clients and nearly 50 implementations among those clients). Our solution automates the manual, burdensome process of submission intake/prep with tools that help triage and prioritize using data from brokers/agents and third-party sources. Our core value propositions (we have production proof points on these) are:
○ Faster, More Data-Driven Underwriting Decisions
○ Unlocking Productivity Gains
○ Improved Broker Responsiveness - which is a key factor in upping win rates
○ Change Management and Increased Employee Buy-In - (very rare in insurance technology)
2) Why would a Top Tier salesperson want to come work at The Company? What was the deciding factor(s) in why you chose to come work at The Company?
● Loves to work on challenging, enterprise sales with confidence that their company and solution can deliver
● Despite selling cutting-edge, innovative solutions, there is an existing client base that adds significant credibility (Travelers, AF Group, WR Berkley companies, Great American companies, Everest, Berkshire Hathaway, Old Republic, JenCap, One80)
● Opportunity to work in a company that uses AI from a firm grounding in data science solutions. We understand we are selling business outcomes; we combine AI, proprietary data models, and human-in-the loop to deliver high quality outcomes to our customers. We don’t sell flash - we sell results.
3) What specific problems in the marketplace does your software or service resolve?
● Operational Inefficiencies & Bottlenecks
○ Data Entry Reduction: Reduced data entry by approximately 65% by pre-populating raters
○ Increased Submission Prep Capacity: Increased submission capacity by 40% without adding headcount
○ Enhanced Underwriter Productivity: Enabled one person to do the work of four.
● Missed Opportunities to Grow Distribution Partner Relationships
● Challenges with Risk Assessment & Profitability
● Technology Fatigue & Adoption Failures
● Drastically Reducing Quote Turnaround Times:
○ Quote Process: Reduced from 20 days to 4 days (an 80% reduction).
○ Loss Run Process: Reduced from 24 hours to 30 minutes (a 97.9% reduction).
○ Submission Completion and Rating Ready: Reduced from 2 days to 2 hours (91.7% reduction).
○ Loss Run & Exposure Entry: Reduced from 3-5 days to just 2-4 hours for All Lines Casualty (over 90% reduction).
○ Increased Quote to Bind Ratio: Increased the quote to bind ratio by over 2x.
4) What kinds of customers/verticals should the Candidate be selling to in order to get an interview?
● LOBs: workers' compensation, commercial auto, GL, and property represent the larger footprint of our solutions.. Also cover professional liability
● Admitted and E&S Carriers along with Large Wholesale MGAs
5) Describe your ideal candidate in your own words.
● We are looking for the person who is going to represent every person in the company to the market. They need to be someone who is going to start what becomes long-term partnerships with clients. We need someone who is going to be proud of building the company and being part of the team.
● Someone who respects and thrives in “the grind”, who is a team player but is self-motivated to the point where they could take something on their shoulders and drag it over the finish line. They understand the insurance industry, how it works, existing workflows (and their inherent pitfalls), and the value chain. They need to be extremely persistent without seeming pushy. Can build relationships quickly, but is patient enough to grow them over time.
● Strong intrinsic traits that make this person successful at whatever it is they’re motivated to pursue:
○ Drive - pursues goals and does not let distractions get in the way
○ Ownership - understands that they own their success and takes responsibility if something doesn’t go according to plan
○ Curious and places a premium on learning new things - figures out how to get around obstacles. Deep Discovery is a strength.
○ Collaborative - can influence and motivate others in a way that team members are happy to support
○ Work ethic - delivers on their daily goals, even if it’s after 5:00
○ Resilience - doesn’t internalize or get sidetracked by a little bad news
6) Why would a Top Tier salesperson want to work for you? Why would they see you as a Mentor?
● Be part of defining and building the business rather than just a salesperson; will be part of decision-making
● Has an actual production solution with real, big names as clients to sell into a nascent area of commercial insurance technology
● The business opportunity to bring AI to insurance in a way that users adopt it and the business sees valuable outcomes
● The Company treats their people right. If someone delivers, they will be happily rewarded.
7) How would you describe The Company's culture?
● We believe in partnership with our clients. We don't overpromise and we deliver. We watch our client's health closely. We show up. We understand what they need to accomplish so we can be part of that journey.
● We our building a company together. Everyone will be behind him as he sells.
● High belief across the business. We know we don't have everything figured out, but we know that we can. The team’s confidence is from the track record of solving complex problems in cross-functional teams. Low voluntary turnover, which is pretty unheard of in a small tech business.
● Collaborative - all voices matter.
8) What does your Marketing Department look like?
● We have a head of Marketing who manages an outside agency and consultants to build our brand awareness and generate MQLs. This setup is relatively new - the agency was hired this spring, and the head of Marketing this summer.
● We are launching a new automated system for BDR activities (Hubsell) this week!
9) Do you use BDRs/SDRs to help with brand awareness/scheduling appointments?
● We are leveraging technology as an automated way of targeting our ICP and personas through email and LinkedIn campaigns to create awareness and set meetings for sales.
10) Last but not least, what is The Company's exit strategy?
● There will come a time when we want to launch a major growth initiative. We will look for funding at that time.
Sales Executive – Property & Casualty Insurance Technology
Location: Remote (U.S. based)
Company offers a platform that enables P&C carriers to win more business and dramatically improve speed to market by transforming the underwriting process.
We are modernizing commercial underwriting by equipping underwriters with smarter workflows, better data, and more time to focus on what matters most, evaluating and selecting risk. Our technology is designed to unlock the full potential of underwriting teams at P&C carriers, MGAs, and wholesalers, and our customers are already seeing measurable results. As we scale, we’re looking for sales professionals who thrive in dynamic environments and want to shape the future of underwriting.
COMPANY has a proven track record with over 50 successful implementations, including seven of the fifteen largest commercial carriers and several major MGAs. The platform delivers results fast, often reaching production go-live within 90 days.
Role Overview
We are looking for a proven and purpose-driven Sales Executive who combines deep P&C organizational and underwriting process knowledge with strong selling skills and the agility to thrive in a high-growth, early-stage environment. You’ll lead complex sales cycles, partner with cross-functional teams, and build trusted relationships with underwriting and technology leaders across the commercial insurance industry.
This role is ideal for someone who sees sales as a craft, seeks continuous improvement, and thrives in environments that reward ownership, curiosity, and impact over ego.
Key Responsibilities
● Own and drive the full sales cycle—from prospecting and discovery through negotiation and close
● Develop a deep understanding of Company’s platform and how it solves real underwriting challenges
● Build relationships with key stakeholders across the business, underwriting, operations, and IT at carriers and MGAs
● Collaborate cross-functionally with marketing, account management, and product teams to shape messaging and ensure successful handoffs
● Act as a thought partner to prospects and be seen as an expert—translating their business goals into clear use cases and value
● Maintain accurate forecasts, pipeline hygiene, and activity tracking in CRM
● Continuously seek ways to improve sales process, messaging, and team performance
Ideal Candidate Profile
Industry & Experience
● Deep understanding of the commercial P&C insurance industry, particularly the underwriting lifecycle and what motivates various leaders who are impacted by underwriting.
● Proven track record of sales success in B2B SaaS or insurance technology
● Experience selling across business units within carriers and MGAs
● Comfortable working in or selling for an emerging growth company
Mindsets & Traits
● Team Player: Collaborative and contributes to making everyone around them better, more efficient, and more committed to the common cause.
● Intrinsic Drive: Motivated by purpose, mastery, and meaningful outcomes—not just quotas
● Extreme Ownership: Takes full accountability for results and course-corrects without excuses
● Curiosity: Probes deeper than the surface, especially in understanding customer needs and internal strategy
● Execution: Delivers consistently, prioritizes ruthlessly, and manages time for impact
● Resilience: Bounces back quickly, remains calm under pressure, and maintains professionalism
● Collaborative but Self-Sufficient: Works well across teams, but doesn’t need handholding
● Strategic Thinking: Understands how their work drives the business and balances short- and long-term outcomes
Why Join Us?
● A mission-driven company at the forefront of transforming a foundational industry
● 8 year track record of delivering successful customer outcomes
● A leadership team with deep expertise and a collaborative mindset
● Room to grow—personally, professionally, and financially—as we scale
● Competitive compensation and equity, along with strong benefits
1) My candidates will be recruited candidates that are happy at the current job and making their numbers, so we have to be able to show them there is a better opportunity at The Company. What is the sizzle around The Company? What does your Solution do for the client?
● The Company is unlocking the promise of AI for P&C Carriers. By leveraging technology, The Company has proven results showing that we enable our customers to:
○ Win more business through faster broker responsiveness and cycle-time reduction
○ Improve risk selection, consistency, and downstream decisioning
○ Get in front of the retiring workforce problem by automating manual tasks and stabilize operations without hiring
● We have 7 of the top 15 commercial carriers as clients - all in production - (with a total of 25 clients and nearly 50 implementations among those clients). Our solution automates the manual, burdensome process of submission intake/prep with tools that help triage and prioritize using data from brokers/agents and third-party sources. Our core value propositions (we have production proof points on these) are:
○ Faster, More Data-Driven Underwriting Decisions
○ Unlocking Productivity Gains
○ Improved Broker Responsiveness - which is a key factor in upping win rates
○ Change Management and Increased Employee Buy-In - (very rare in insurance technology)
2) Why would a Top Tier salesperson want to come work at The Company? What was the deciding factor(s) in why you chose to come work at The Company?
● Loves to work on challenging, enterprise sales with confidence that their company and solution can deliver
● Despite selling cutting-edge, innovative solutions, there is an existing client base that adds significant credibility (Travelers, AF Group, WR Berkley companies, Great American companies, Everest, Berkshire Hathaway, Old Republic, JenCap, One80)
● Opportunity to work in a company that uses AI from a firm grounding in data science solutions. We understand we are selling business outcomes; we combine AI, proprietary data models, and human-in-the loop to deliver high quality outcomes to our customers. We don’t sell flash - we sell results.
3) What specific problems in the marketplace does your software or service resolve?
● Operational Inefficiencies & Bottlenecks
○ Data Entry Reduction: Reduced data entry by approximately 65% by pre-populating raters
○ Increased Submission Prep Capacity: Increased submission capacity by 40% without adding headcount
○ Enhanced Underwriter Productivity: Enabled one person to do the work of four.
● Missed Opportunities to Grow Distribution Partner Relationships
● Challenges with Risk Assessment & Profitability
● Technology Fatigue & Adoption Failures
● Drastically Reducing Quote Turnaround Times:
○ Quote Process: Reduced from 20 days to 4 days (an 80% reduction).
○ Loss Run Process: Reduced from 24 hours to 30 minutes (a 97.9% reduction).
○ Submission Completion and Rating Ready: Reduced from 2 days to 2 hours (91.7% reduction).
○ Loss Run & Exposure Entry: Reduced from 3-5 days to just 2-4 hours for All Lines Casualty (over 90% reduction).
○ Increased Quote to Bind Ratio: Increased the quote to bind ratio by over 2x.
4) What kinds of customers/verticals should the Candidate be selling to in order to get an interview?
● LOBs: workers' compensation, commercial auto, GL, and property represent the larger footprint of our solutions.. Also cover professional liability
● Admitted and E&S Carriers along with Large Wholesale MGAs
5) Describe your ideal candidate in your own words.
● We are looking for the person who is going to represent every person in the company to the market. They need to be someone who is going to start what becomes long-term partnerships with clients. We need someone who is going to be proud of building the company and being part of the team.
● Someone who respects and thrives in “the grind”, who is a team player but is self-motivated to the point where they could take something on their shoulders and drag it over the finish line. They understand the insurance industry, how it works, existing workflows (and their inherent pitfalls), and the value chain. They need to be extremely persistent without seeming pushy. Can build relationships quickly, but is patient enough to grow them over time.
● Strong intrinsic traits that make this person successful at whatever it is they’re motivated to pursue:
○ Drive - pursues goals and does not let distractions get in the way
○ Ownership - understands that they own their success and takes responsibility if something doesn’t go according to plan
○ Curious and places a premium on learning new things - figures out how to get around obstacles. Deep Discovery is a strength.
○ Collaborative - can influence and motivate others in a way that team members are happy to support
○ Work ethic - delivers on their daily goals, even if it’s after 5:00
○ Resilience - doesn’t internalize or get sidetracked by a little bad news
6) Why would a Top Tier salesperson want to work for you? Why would they see you as a Mentor?
● Be part of defining and building the business rather than just a salesperson; will be part of decision-making
● Has an actual production solution with real, big names as clients to sell into a nascent area of commercial insurance technology
● The business opportunity to bring AI to insurance in a way that users adopt it and the business sees valuable outcomes
● The Company treats their people right. If someone delivers, they will be happily rewarded.
7) How would you describe The Company's culture?
● We believe in partnership with our clients. We don't overpromise and we deliver. We watch our client's health closely. We show up. We understand what they need to accomplish so we can be part of that journey.
● We our building a company together. Everyone will be behind him as he sells.
● High belief across the business. We know we don't have everything figured out, but we know that we can. The team’s confidence is from the track record of solving complex problems in cross-functional teams. Low voluntary turnover, which is pretty unheard of in a small tech business.
● Collaborative - all voices matter.
8) What does your Marketing Department look like?
● We have a head of Marketing who manages an outside agency and consultants to build our brand awareness and generate MQLs. This setup is relatively new - the agency was hired this spring, and the head of Marketing this summer.
● We are launching a new automated system for BDR activities (Hubsell) this week!
9) Do you use BDRs/SDRs to help with brand awareness/scheduling appointments?
● We are leveraging technology as an automated way of targeting our ICP and personas through email and LinkedIn campaigns to create awareness and set meetings for sales.
10) Last but not least, what is The Company's exit strategy?
● There will come a time when we want to launch a major growth initiative. We will look for funding at that time.
Sales Executive – Property & Casualty Insurance Technology
Location: Remote (U.S. based)
Company offers a platform that enables P&C carriers to win more business and dramatically improve speed to market by transforming the underwriting process.
We are modernizing commercial underwriting by equipping underwriters with smarter workflows, better data, and more time to focus on what matters most, evaluating and selecting risk. Our technology is designed to unlock the full potential of underwriting teams at P&C carriers, MGAs, and wholesalers, and our customers are already seeing measurable results. As we scale, we’re looking for sales professionals who thrive in dynamic environments and want to shape the future of underwriting.
COMPANY has a proven track record with over 50 successful implementations, including seven of the fifteen largest commercial carriers and several major MGAs. The platform delivers results fast, often reaching production go-live within 90 days.
Role Overview
We are looking for a proven and purpose-driven Sales Executive who combines deep P&C organizational and underwriting process knowledge with strong selling skills and the agility to thrive in a high-growth, early-stage environment. You’ll lead complex sales cycles, partner with cross-functional teams, and build trusted relationships with underwriting and technology leaders across the commercial insurance industry.
This role is ideal for someone who sees sales as a craft, seeks continuous improvement, and thrives in environments that reward ownership, curiosity, and impact over ego.
Key Responsibilities
● Own and drive the full sales cycle—from prospecting and discovery through negotiation and close
● Develop a deep understanding of Company’s platform and how it solves real underwriting challenges
● Build relationships with key stakeholders across the business, underwriting, operations, and IT at carriers and MGAs
● Collaborate cross-functionally with marketing, account management, and product teams to shape messaging and ensure successful handoffs
● Act as a thought partner to prospects and be seen as an expert—translating their business goals into clear use cases and value
● Maintain accurate forecasts, pipeline hygiene, and activity tracking in CRM
● Continuously seek ways to improve sales process, messaging, and team performance
Ideal Candidate Profile
Industry & Experience
● Deep understanding of the commercial P&C insurance industry, particularly the underwriting lifecycle and what motivates various leaders who are impacted by underwriting.
● Proven track record of sales success in B2B SaaS or insurance technology
● Experience selling across business units within carriers and MGAs
● Comfortable working in or selling for an emerging growth company
Mindsets & Traits
● Team Player: Collaborative and contributes to making everyone around them better, more efficient, and more committed to the common cause.
● Intrinsic Drive: Motivated by purpose, mastery, and meaningful outcomes—not just quotas
● Extreme Ownership: Takes full accountability for results and course-corrects without excuses
● Curiosity: Probes deeper than the surface, especially in understanding customer needs and internal strategy
● Execution: Delivers consistently, prioritizes ruthlessly, and manages time for impact
● Resilience: Bounces back quickly, remains calm under pressure, and maintains professionalism
● Collaborative but Self-Sufficient: Works well across teams, but doesn’t need handholding
● Strategic Thinking: Understands how their work drives the business and balances short- and long-term outcomes
Why Join Us?
● A mission-driven company at the forefront of transforming a foundational industry
● 8 year track record of delivering successful customer outcomes
● A leadership team with deep expertise and a collaborative mindset
● Room to grow—personally, professionally, and financially—as we scale
● Competitive compensation and equity, along with strong benefits