VP of Sales, Health Insurance Vertical
Gradient AI · Boston, MA · 1 mo ago
RemoteRemoteBusiness Development$56/hrFull-time
We need to output HTML fragment with sections: About the role, Responsibilities? Actually the posting includes "About the Role" then "How You Will Make an Impact" (responsibilities), "Skills Needed to Succeed" (requirements/qualifications/skills), "What We Offer" (benefits), and OTE range (pay). Also mention fully remote opportunity (schedule? remote). We need to use for section headings. No repeated job title. No Job ID. Remove boilerplate like EEO, equal opportunity, etc. Also remove "We are an equal opportunity employer." Also remove "In accordance with the Massachusetts Pay Transparency Law..." maybe keep OTE range but not the legal text? The instruction: remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. The OTE range is substantive; we can keep it but maybe we need to put under Pay section. The legal text about Massachusetts Pay Transparency Law is legal boilerplate; we should remove it. Also "If your salary expectations fall outside this range, we still encourage you to apply..." is application instruction? Might be considered boilerplate; we can drop.
We need to include sections only when posting has real specific content. So we will have:
for section headings. No repeated job title. No Job ID. Remove boilerplate like EEO, equal opportunity, etc. Also remove "We are an equal opportunity employer." Also remove "In accordance with the Massachusetts Pay Transparency Law..." maybe keep OTE range but not the legal text? The instruction: remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. The OTE range is substantive; we can keep it but maybe we need to put under Pay section. The legal text about Massachusetts Pay Transparency Law is legal boilerplate; we should remove it. Also "If your salary expectations fall outside this range, we still encourage you to apply..." is application instruction? Might be considered boilerplate; we can drop.
We need to include sections only when posting has real specific content. So we will have:
About the role
with paragraph(s) describing role.
How You Will Make an Impact
with - list of responsibilities.
Skills Needed to Succeed
with - list of skills/requirements.
What We Offer
with - list of benefits.
Pay
with paragraph containing OTE range: $500k OTE inclusive of base salary with strong accelerators, also commission, equity grant, comprehensive benefits package.
Schedule: remote opportunity, flexible schedule that supports working from home. Could be under Schedule section. The posting says "This is a fully remote opportunity." and "Flexible schedule that supports working from home." So we can create a Schedule section with that info.
We must not create sections with filler like "commensurate with experience". We have actual content.
We need to preserve all substantive information; do not invent or summarize away detail. So we need to include all bullet points from "How You Will Make an Impact" and "Skills Needed to Succeed" and "What We Offer". Also include the description of Gradient AI at top? The first paragraph about company is substantive; we could include it maybe under About the role? But the instruction: "About the role" heading is for section headings. The initial company description could be placed before any heading as a . It's not a heading. So we can start with a paragraph describing Gradient AI. Then
About the role
with paragraph about role.
We must not repeat the job title as a heading. The job title is "VP of Enterprise Sales". Not to be used as heading.
We must not put Job ID/requisition numbers as headings; none present.
We must output only HTML fragment, no /, no markdown fences.
Let's extract details.
Company description:
"This is a fully remote opportunity. Gradient AI: Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry's largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team."
We need to keep "This is a fully remote opportunity." as part of description.
Now About the role paragraph:
"We are searching for a results-driven VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. In this role, you'll own your team's pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick. They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team's results to leadership."
Now How You Will Make an Impact bullet list:
- Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards
- Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce
- Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative
- Lead by example on key deals, stepping into complex or strategic opportunities to model consultative selling and build credibility with major accounts
- Own hiring, onboarding, and ramp planning for new reps joining the team
- Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team
- Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging
- Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities
Now Skills Needed to Succeed bullet list:
- 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team
- Domain expertise in the health insurance space
- Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance
- A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team
- Ideally prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations
- Outstanding verbal and written communication skills
- Ability to lead in a self-driven manner within a fast-paced, collaborative startup environment; comfort with ambiguity and a bias toward action
Now What We Offer bullet list:
- A fun, team-oriented startup culture.
- Generous stock options - we all get to own a piece of what we're building.
- Unlimited vacation days.
- Flexible schedule that supports working from home.
- Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more.
- Ample opportunities to learn and take on new responsibilities.
Now Pay section: OTE range: "The anticipated on-target earnings (OTE) for this position is $500k, inclusive of base salary with strong accelerators. This role is also eligible for commission, equity grant and a comprehensive benefits package."
We might also mention that compensation may grow over time etc but that's somewhat generic; we could include but it's not specific numbers. Might be okay to include as part of Pay paragraph.
Schedule section: we already have flexible schedule in benefits; but we could also have a Schedule section stating "Fully remote opportunity. Flexible schedule that supports working from home." However we already have flexible schedule in benefits; but we can still have Schedule section with remote info. The instruction: prefer a few substantive sections over many thin ones. We could combine remote/flexible schedule into Benefits or Schedule. Since we already have Benefits section includes flexible schedule, we could omit separate Schedule section. But we have "This is a fully remote opportunity." which is not a benefit but a work arrangement. Could be part of Benefits or a separate Schedule. Since we already have Benefits includes flexible schedule, we could add remote note there. But we need to preserve all substantive information; we can include remote in Benefits bullet list as "Fully remote opportunity." or as separate bullet. Let's add a bullet under What We Offer: "Fully remote opportunity." However the benefits list already had "Flexible schedule that supports working from home." which is similar but not exactly remote. We'll add both.
Thus What We Offer bullets:
- A fun, team-oriented startup culture.
- Generous stock options - we all get to own a piece of what we're building.
- Unlimited vacation days.
- Fully remote opportunity.
- Flexible schedule that supports working from home.
- Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more.
- Ample opportunities to learn and take on new responsibilities.
Now Pay section paragraph.
We must not include legal boilerplate about Massachusetts Pay Transparency Law etc. So we will omit that.
Now ensure we don't duplicate lines. The posting had "We are an equal opportunity employer." We'll drop.
Now produce HTML.
Structure:
This is a fully remote opportunity. Gradient AI: Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry's largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.
About the role
We are searching for a results-driven VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. In this role, you'll own your team's pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick. They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team's results to leadership.
How You Will Make an Impact
- Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards
- Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce
- Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative
- Lead by example on key deals, stepping into complex or strategic opportunities to model consultative selling and build credibility with major accounts
- Own hiring, onboarding, and ramp planning for new reps joining the team
- Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team
- Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging
- Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities
Skills Needed to Succeed
- 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team
- Domain expertise in the health insurance space
- Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance
- A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team
- Ideally prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations
- Outstanding verbal and written communication skills
- Ability to lead in a self-driven manner within a fast-p
Skills Needed to Succeed
with- list of skills/requirements.
What We Offer
with- list of benefits.
Pay
with paragraph containing OTE range: $500k OTE inclusive of base salary with strong accelerators, also commission, equity grant, comprehensive benefits package. Schedule: remote opportunity, flexible schedule that supports working from home. Could be under Schedule section. The posting says "This is a fully remote opportunity." and "Flexible schedule that supports working from home." So we can create a Schedule section with that info. We must not create sections with filler like "commensurate with experience". We have actual content. We need to preserve all substantive information; do not invent or summarize away detail. So we need to include all bullet points from "How You Will Make an Impact" and "Skills Needed to Succeed" and "What We Offer". Also include the description of Gradient AI at top? The first paragraph about company is substantive; we could include it maybe under About the role? But the instruction: "About the role" heading is for section headings. The initial company description could be placed before any heading as a. It's not a heading. So we can start with a paragraph describing Gradient AI. Then
About the role
with paragraph about role. We must not repeat the job title as a heading. The job title is "VP of Enterprise Sales". Not to be used as heading. We must not put Job ID/requisition numbers as headings; none present. We must output only HTML fragment, no /, no markdown fences. Let's extract details. Company description: "This is a fully remote opportunity. Gradient AI: Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry's largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team." We need to keep "This is a fully remote opportunity." as part of description. Now About the role paragraph: "We are searching for a results-driven VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. In this role, you'll own your team's pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick. They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team's results to leadership." Now How You Will Make an Impact bullet list: - Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards - Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce - Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative - Lead by example on key deals, stepping into complex or strategic opportunities to model consultative selling and build credibility with major accounts - Own hiring, onboarding, and ramp planning for new reps joining the team - Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team - Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging - Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities Now Skills Needed to Succeed bullet list: - 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team - Domain expertise in the health insurance space - Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance - A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team - Ideally prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations - Outstanding verbal and written communication skills - Ability to lead in a self-driven manner within a fast-paced, collaborative startup environment; comfort with ambiguity and a bias toward action Now What We Offer bullet list: - A fun, team-oriented startup culture. - Generous stock options - we all get to own a piece of what we're building. - Unlimited vacation days. - Flexible schedule that supports working from home. - Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more. - Ample opportunities to learn and take on new responsibilities. Now Pay section: OTE range: "The anticipated on-target earnings (OTE) for this position is $500k, inclusive of base salary with strong accelerators. This role is also eligible for commission, equity grant and a comprehensive benefits package." We might also mention that compensation may grow over time etc but that's somewhat generic; we could include but it's not specific numbers. Might be okay to include as part of Pay paragraph. Schedule section: we already have flexible schedule in benefits; but we could also have a Schedule section stating "Fully remote opportunity. Flexible schedule that supports working from home." However we already have flexible schedule in benefits; but we can still have Schedule section with remote info. The instruction: prefer a few substantive sections over many thin ones. We could combine remote/flexible schedule into Benefits or Schedule. Since we already have Benefits section includes flexible schedule, we could omit separate Schedule section. But we have "This is a fully remote opportunity." which is not a benefit but a work arrangement. Could be part of Benefits or a separate Schedule. Since we already have Benefits includes flexible schedule, we could add remote note there. But we need to preserve all substantive information; we can include remote in Benefits bullet list as "Fully remote opportunity." or as separate bullet. Let's add a bullet under What We Offer: "Fully remote opportunity." However the benefits list already had "Flexible schedule that supports working from home." which is similar but not exactly remote. We'll add both. Thus What We Offer bullets: - A fun, team-oriented startup culture. - Generous stock options - we all get to own a piece of what we're building. - Unlimited vacation days. - Fully remote opportunity. - Flexible schedule that supports working from home. - Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more. - Ample opportunities to learn and take on new responsibilities. Now Pay section paragraph. We must not include legal boilerplate about Massachusetts Pay Transparency Law etc. So we will omit that. Now ensure we don't duplicate lines. The posting had "We are an equal opportunity employer." We'll drop. Now produce HTML. Structure:This is a fully remote opportunity. Gradient AI: Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry's largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.
About the role
We are searching for a results-driven VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. In this role, you'll own your team's pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick. They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team's results to leadership.
How You Will Make an Impact
- Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards
- Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce
- Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative
- Lead by example on key deals, stepping into complex or strategic opportunities to model consultative selling and build credibility with major accounts
- Own hiring, onboarding, and ramp planning for new reps joining the team
- Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team
- Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging
- Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities
Skills Needed to Succeed
- 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team
- Domain expertise in the health insurance space
- Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance
- A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team
- Ideally prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations
- Outstanding verbal and written communication skills
- Ability to lead in a self-driven manner within a fast-p
- list of benefits.