Customer Service Operations Specialist
for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). Use - for any list of duties/requirements/benefits, and
for prose. Do NOT repeat the job title as a heading. Do NOT put Job ID / requisition numbers as headings — fold minor metadata into a short
or drop it. Preserve ALL substantive information; do NOT invent or summarize away detail. Remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. IMPORTANT: include a section ONLY when the posting has real, specific content for it — never emit a heading followed by filler/placeholder text (e.g. "commensurate with experience", "not specified", "N/A", "varies", "TBD") and never create Pay/Schedule/Benefits sections unless the posting actually states them. Prefer a few substantive sections over many thin ones. Output ONLY the HTML fragment — no /, no markdown code fences.
Thus we need to decide which sections to include. Likely: About the role (maybe from The Role paragraph), Responsibilities (What You'll Do), Requirements, Qualifications (maybe Nice to Have?), Skills (maybe not explicit), Benefits, Pay (Compensation), Schedule.
We must not invent sections if content not present. Let's extract content.
The posting:
- The Problem (intro) - maybe not needed as a section; but we could incorporate into About the role? The instruction says use headings like About the role, Responsibilities, etc. The Problem is not one of those headings; we could maybe omit it or incorporate into About the role? But we must preserve ALL substantive information. If we omit The Problem, we lose info. However we could include it as a
before any heading? The instruction says output ONLY the HTML fragment; we can include paragraphs not under headings? It didn't forbid that. It says use
for section headings (e.g. About the role, Responsibilities...). Use - for any list... and
for prose. It doesn't say we must wrap everything in headings. So we can have leading paragraphs before first heading. That's okay.
Thus we can keep The Problem as a
(or multiple
) before first heading.
Similarly The Thesis could be a
.
Then we can have
About the role
with content from The Role paragraph.
Then Responsibilities
with list from What You'll Do.
Then Requirements
with list from Requirements.
Then Qualifications
maybe from Nice to Have? Or we could treat Nice to Have as Qualifications. The instruction includes Qualifications as a possible heading. We'll use that for Nice to Have.
Then Skills
maybe not present; we could omit if no specific skills list. There's mention of "Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short" - that's a skill but could be part of Requirements. We might not need separate Skills.
Then Benefits
with list from Benefits.
Then Pay
with compensation details.
Then Schedule
with schedule details.
We also have Location and Process and To Apply (application instructions) which we should remove per instruction: remove application instructions. Also remove duplicated lines. So we should omit The Process and To Apply sections.
Also we need to preserve all substantive information; we must keep location info? The posting includes Location: San Francisco, Atlanta, or New York City, in-office. That's substantive. Should we include it? Possibly under About the role or as a separate . Since we have no heading for Location, we can include as a
after Pay or before Benefits. The instruction says we can use
for prose. So we can add a
for Location.
Similarly we have Start date: Immediate. That's also substantive; we can include as a
.
We must not include duplicated lines. Ensure we don't repeat.
Now let's extract content precisely.
The Problem paragraph:
"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'll keep as
.
The Thesis paragraph:
"The Thesis Commercial insurance gets complicated fast. A business opens a second location, wins a contract with insurance requirements it doesn't currently meet, adds a fleet, gets hit with a premium audit, grows out of the market it started in, or needs coverage that doesn't exist on a standard form. Those accounts don't need a queue. They need somebody with deep expertise and the latitude to act on it. That's this team. You take the accounts that call for real judgment, you work them directly with the underwriters and wholesalers, and you stay on them until the customer has an answer. Then your expertise becomes the playbook the rest of the service organization runs on, which is how a small team serves a book growing this fast. We're also building this tier now rather than handing you someone else's version of it. Harper's long-term plan puts service at the center of the company—expertise, retention and revenue all living in one organization—and the specialists we hire first will shape what that looks like."
We'll keep as
.
The Role paragraph:
"The Role You own our most complex accounts and the hardest customer situations. Premium audits and inspection recommendations that carry real deadlines. Renewals worth remarketing to get a business better terms. E&S and surplus lines placements, with the filings and binding packets that come with them. Premium finance arrangements and the paperwork behind them. Coverage questions that need someone who can read a policy form and a contract and explain what's actually covered. And the accounts at risk of cancellation, where somebody's coverage is genuinely on the line and a customer needs a person who will solve it. You own relationships too. Every underwriter and wholesaler we work with has a named owner on this team, and you'll be one of them. You're the person they pick up the phone for—and the person who can get a real answer for a customer because you've built that credibility over years. You're the last stop inside service, which means nothing you pick up gets handed to somebody else to figure out. You have the latitude to make the call, and when something genuinely needs a founder's decision you bring it to them with your recommendation attached. Complex cases get answers in days here, not weeks."
We'll put under
About the role
as prose ().
What You'll Do bullet list:
- Own the complex accounts end to end — The situations that need experience rather than a script; you keep them until the customer has a real answer
- Work the markets on your customers' behalf — Partner with underwriters and wholesalers to place hard risks, remarket renewals for better terms, and find a home for businesses standard markets won't write
- Guide customers through audits and inspections — Premium audits, payroll and sales verification, inspection recommendations with deadlines; make sure the final number and the required changes are right and understood
- Handle E&S and surplus lines work — Eligibility, filings, surplus lines tax, binding packets, and the documentation that has to be correct the first time
- Make coverage match the business — Businesses change constantly: new locations, vehicles, payroll, equipment, and contracts with new requirements; keep coverage, class codes and records current as they grow
- Save accounts worth saving — Work payment, financing and cancellation situations with the customer and the finance company so coverage stays in force
- Be the name your carriers know — Own specific underwriter and wholesaler relationships and build the kind of credibility that gets customers a better outcome
- Level up the team around you — Turn what you know into playbooks, train the service team, and grow the tier-two group into people who can handle more every month
- Make the system smarter — Work in our service workbench daily and tell Product and Engineering what to automate, so your expertise scales past your own calendar
We'll put under
Responsibilities
as - ...
You Might Be a Fit If... bullet list:
- You're the person colleagues bring the case nobody else can crack
- You have real relationships with underwriters and wholesalers—and they take your call
- You'd rather decide with the facts you have and document your reasoning than let an account sit for three weeks
- You're tired of needing three approvals to do the obviously right thing
- You can hold a case open for days without losing the thread, and keep twenty of them straight
- You're curious about AI tools and want to tell engineers what to build, not wait for permission
- You want to build this function, not inherit someone else's version of it
- You know startup pace is a real adjustment from a traditional brokerage and you want it anyway
We could treat this as maybe Skills or Qualities. But instruction only lists certain headings; we could omit this section if not matching headings. However it's substantive. Could we put under
Skills
? The list includes traits like "curious about AI tools", "want to build this function". Those could be considered skills or qualities. We'll include as Skills
with .
Requirements list:
- 5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side roles
- Active property & casualty license—we handle non-resident and reciprocal licensing across all 50 states
- Existing carrier and wholesaler relationships you can put to work
- A track record owning complex commercial cases end to end, not just triaging them
- Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short
- Based in New York City or San Francisco, or willing to relocate; this role is in-office
We'll put under Requirements
as .
Nice to Have list:
- Surplus lines license
- E&S experience: surplus lines tax, filings, binding packets, DocuSign workflows
- Premium finance depth: PFAs, reconciliation, finance-company defaults and cancellation reversals
- Workers' comp and class-code expertise, including NCCI audit disputes
- Wholesaler, MGA or carrier underwriting-desk background
- Experience at an insurtech or tech-forward brokerage
We'll put under Qualifications
as .
Compensation:
"Compensation Salary: $110,000–$150,000 + performance bonuses + equityLocation: San Francisco, Atlanta, or
for prose. Do NOT repeat the job title as a heading. Do NOT put Job ID / requisition numbers as headings — fold minor metadata into a short
or drop it. Preserve ALL substantive information; do NOT invent or summarize away detail. Remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. IMPORTANT: include a section ONLY when the posting has real, specific content for it — never emit a heading followed by filler/placeholder text (e.g. "commensurate with experience", "not specified", "N/A", "varies", "TBD") and never create Pay/Schedule/Benefits sections unless the posting actually states them. Prefer a few substantive sections over many thin ones. Output ONLY the HTML fragment — no /, no markdown code fences. Thus we need to decide which sections to include. Likely: About the role (maybe from The Role paragraph), Responsibilities (What You'll Do), Requirements, Qualifications (maybe Nice to Have?), Skills (maybe not explicit), Benefits, Pay (Compensation), Schedule. We must not invent sections if content not present. Let's extract content. The posting: - The Problem (intro) - maybe not needed as a section; but we could incorporate into About the role? The instruction says use headings like About the role, Responsibilities, etc. The Problem is not one of those headings; we could maybe omit it or incorporate into About the role? But we must preserve ALL substantive information. If we omit The Problem, we lose info. However we could include it as a
before any heading? The instruction says output ONLY the HTML fragment; we can include paragraphs not under headings? It didn't forbid that. It says use
for section headings (e.g. About the role, Responsibilities...). Use - for any list... and
for prose. It doesn't say we must wrap everything in headings. So we can have leading paragraphs before first heading. That's okay.
Thus we can keep The Problem as a
(or multiple
) before first heading.
Similarly The Thesis could be a
.
Then we can have
About the role
with content from The Role paragraph.
Then Responsibilities
with list from What You'll Do.
Then Requirements
with list from Requirements.
Then Qualifications
maybe from Nice to Have? Or we could treat Nice to Have as Qualifications. The instruction includes Qualifications as a possible heading. We'll use that for Nice to Have.
Then Skills
maybe not present; we could omit if no specific skills list. There's mention of "Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short" - that's a skill but could be part of Requirements. We might not need separate Skills.
Then Benefits
with list from Benefits.
Then Pay
with compensation details.
Then Schedule
with schedule details.
We also have Location and Process and To Apply (application instructions) which we should remove per instruction: remove application instructions. Also remove duplicated lines. So we should omit The Process and To Apply sections.
Also we need to preserve all substantive information; we must keep location info? The posting includes Location: San Francisco, Atlanta, or New York City, in-office. That's substantive. Should we include it? Possibly under About the role or as a separate . Since we have no heading for Location, we can include as a
after Pay or before Benefits. The instruction says we can use
for prose. So we can add a
for Location.
Similarly we have Start date: Immediate. That's also substantive; we can include as a
.
We must not include duplicated lines. Ensure we don't repeat.
Now let's extract content precisely.
The Problem paragraph:
"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'll keep as
.
The Thesis paragraph:
"The Thesis Commercial insurance gets complicated fast. A business opens a second location, wins a contract with insurance requirements it doesn't currently meet, adds a fleet, gets hit with a premium audit, grows out of the market it started in, or needs coverage that doesn't exist on a standard form. Those accounts don't need a queue. They need somebody with deep expertise and the latitude to act on it. That's this team. You take the accounts that call for real judgment, you work them directly with the underwriters and wholesalers, and you stay on them until the customer has an answer. Then your expertise becomes the playbook the rest of the service organization runs on, which is how a small team serves a book growing this fast. We're also building this tier now rather than handing you someone else's version of it. Harper's long-term plan puts service at the center of the company—expertise, retention and revenue all living in one organization—and the specialists we hire first will shape what that looks like."
We'll keep as
.
The Role paragraph:
"The Role You own our most complex accounts and the hardest customer situations. Premium audits and inspection recommendations that carry real deadlines. Renewals worth remarketing to get a business better terms. E&S and surplus lines placements, with the filings and binding packets that come with them. Premium finance arrangements and the paperwork behind them. Coverage questions that need someone who can read a policy form and a contract and explain what's actually covered. And the accounts at risk of cancellation, where somebody's coverage is genuinely on the line and a customer needs a person who will solve it. You own relationships too. Every underwriter and wholesaler we work with has a named owner on this team, and you'll be one of them. You're the person they pick up the phone for—and the person who can get a real answer for a customer because you've built that credibility over years. You're the last stop inside service, which means nothing you pick up gets handed to somebody else to figure out. You have the latitude to make the call, and when something genuinely needs a founder's decision you bring it to them with your recommendation attached. Complex cases get answers in days here, not weeks."
We'll put under
About the role
as prose ().
What You'll Do bullet list:
- Own the complex accounts end to end — The situations that need experience rather than a script; you keep them until the customer has a real answer
- Work the markets on your customers' behalf — Partner with underwriters and wholesalers to place hard risks, remarket renewals for better terms, and find a home for businesses standard markets won't write
- Guide customers through audits and inspections — Premium audits, payroll and sales verification, inspection recommendations with deadlines; make sure the final number and the required changes are right and understood
- Handle E&S and surplus lines work — Eligibility, filings, surplus lines tax, binding packets, and the documentation that has to be correct the first time
- Make coverage match the business — Businesses change constantly: new locations, vehicles, payroll, equipment, and contracts with new requirements; keep coverage, class codes and records current as they grow
- Save accounts worth saving — Work payment, financing and cancellation situations with the customer and the finance company so coverage stays in force
- Be the name your carriers know — Own specific underwriter and wholesaler relationships and build the kind of credibility that gets customers a better outcome
- Level up the team around you — Turn what you know into playbooks, train the service team, and grow the tier-two group into people who can handle more every month
- Make the system smarter — Work in our service workbench daily and tell Product and Engineering what to automate, so your expertise scales past your own calendar
We'll put under
Responsibilities
as - ...
You Might Be a Fit If... bullet list:
- You're the person colleagues bring the case nobody else can crack
- You have real relationships with underwriters and wholesalers—and they take your call
- You'd rather decide with the facts you have and document your reasoning than let an account sit for three weeks
- You're tired of needing three approvals to do the obviously right thing
- You can hold a case open for days without losing the thread, and keep twenty of them straight
- You're curious about AI tools and want to tell engineers what to build, not wait for permission
- You want to build this function, not inherit someone else's version of it
- You know startup pace is a real adjustment from a traditional brokerage and you want it anyway
We could treat this as maybe Skills or Qualities. But instruction only lists certain headings; we could omit this section if not matching headings. However it's substantive. Could we put under
Skills
? The list includes traits like "curious about AI tools", "want to build this function". Those could be considered skills or qualities. We'll include as Skills
with .
Requirements list:
- 5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side roles
- Active property & casualty license—we handle non-resident and reciprocal licensing across all 50 states
- Existing carrier and wholesaler relationships you can put to work
- A track record owning complex commercial cases end to end, not just triaging them
- Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short
- Based in New York City or San Francisco, or willing to relocate; this role is in-office
We'll put under Requirements
as .
Nice to Have list:
- Surplus lines license
- E&S experience: surplus lines tax, filings, binding packets, DocuSign workflows
- Premium finance depth: PFAs, reconciliation, finance-company defaults and cancellation reversals
- Workers' comp and class-code expertise, including NCCI audit disputes
- Wholesaler, MGA or carrier underwriting-desk background
- Experience at an insurtech or tech-forward brokerage
We'll put under Qualifications
as .
Compensation:
"Compensation Salary: $110,000–$150,000 + performance bonuses + equityLocation: San Francisco, Atlanta, or
for prose. It doesn't say we must wrap everything in headings. So we can have leading paragraphs before first heading. That's okay. Thus we can keep The Problem as a
(or multiple
) before first heading. Similarly The Thesis could be a
. Then we can have
About the role
with content from The Role paragraph. ThenResponsibilities
with list from What You'll Do. ThenRequirements
with list from Requirements. ThenQualifications
maybe from Nice to Have? Or we could treat Nice to Have as Qualifications. The instruction includes Qualifications as a possible heading. We'll use that for Nice to Have. ThenSkills
maybe not present; we could omit if no specific skills list. There's mention of "Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short" - that's a skill but could be part of Requirements. We might not need separate Skills. ThenBenefits
with list from Benefits. ThenPay
with compensation details. ThenSchedule
with schedule details. We also have Location and Process and To Apply (application instructions) which we should remove per instruction: remove application instructions. Also remove duplicated lines. So we should omit The Process and To Apply sections. Also we need to preserve all substantive information; we must keep location info? The posting includes Location: San Francisco, Atlanta, or New York City, in-office. That's substantive. Should we include it? Possibly under About the role or as a separate. Since we have no heading for Location, we can include as a
after Pay or before Benefits. The instruction says we can use
for prose. So we can add a
for Location. Similarly we have Start date: Immediate. That's also substantive; we can include as a
. We must not include duplicated lines. Ensure we don't repeat. Now let's extract content precisely. The Problem paragraph: "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'll keep as
. The Thesis paragraph: "The Thesis Commercial insurance gets complicated fast. A business opens a second location, wins a contract with insurance requirements it doesn't currently meet, adds a fleet, gets hit with a premium audit, grows out of the market it started in, or needs coverage that doesn't exist on a standard form. Those accounts don't need a queue. They need somebody with deep expertise and the latitude to act on it. That's this team. You take the accounts that call for real judgment, you work them directly with the underwriters and wholesalers, and you stay on them until the customer has an answer. Then your expertise becomes the playbook the rest of the service organization runs on, which is how a small team serves a book growing this fast. We're also building this tier now rather than handing you someone else's version of it. Harper's long-term plan puts service at the center of the company—expertise, retention and revenue all living in one organization—and the specialists we hire first will shape what that looks like." We'll keep as
. The Role paragraph: "The Role You own our most complex accounts and the hardest customer situations. Premium audits and inspection recommendations that carry real deadlines. Renewals worth remarketing to get a business better terms. E&S and surplus lines placements, with the filings and binding packets that come with them. Premium finance arrangements and the paperwork behind them. Coverage questions that need someone who can read a policy form and a contract and explain what's actually covered. And the accounts at risk of cancellation, where somebody's coverage is genuinely on the line and a customer needs a person who will solve it. You own relationships too. Every underwriter and wholesaler we work with has a named owner on this team, and you'll be one of them. You're the person they pick up the phone for—and the person who can get a real answer for a customer because you've built that credibility over years. You're the last stop inside service, which means nothing you pick up gets handed to somebody else to figure out. You have the latitude to make the call, and when something genuinely needs a founder's decision you bring it to them with your recommendation attached. Complex cases get answers in days here, not weeks." We'll put under
About the role
as prose (). What You'll Do bullet list: - Own the complex accounts end to end — The situations that need experience rather than a script; you keep them until the customer has a real answer - Work the markets on your customers' behalf — Partner with underwriters and wholesalers to place hard risks, remarket renewals for better terms, and find a home for businesses standard markets won't write - Guide customers through audits and inspections — Premium audits, payroll and sales verification, inspection recommendations with deadlines; make sure the final number and the required changes are right and understood - Handle E&S and surplus lines work — Eligibility, filings, surplus lines tax, binding packets, and the documentation that has to be correct the first time - Make coverage match the business — Businesses change constantly: new locations, vehicles, payroll, equipment, and contracts with new requirements; keep coverage, class codes and records current as they grow - Save accounts worth saving — Work payment, financing and cancellation situations with the customer and the finance company so coverage stays in force - Be the name your carriers know — Own specific underwriter and wholesaler relationships and build the kind of credibility that gets customers a better outcome - Level up the team around you — Turn what you know into playbooks, train the service team, and grow the tier-two group into people who can handle more every month - Make the system smarter — Work in our service workbench daily and tell Product and Engineering what to automate, so your expertise scales past your own calendar We'll put under
Responsibilities
as- ...
You Might Be a Fit If... bullet list:
- You're the person colleagues bring the case nobody else can crack
- You have real relationships with underwriters and wholesalers—and they take your call
- You'd rather decide with the facts you have and document your reasoning than let an account sit for three weeks
- You're tired of needing three approvals to do the obviously right thing
- You can hold a case open for days without losing the thread, and keep twenty of them straight
- You're curious about AI tools and want to tell engineers what to build, not wait for permission
- You want to build this function, not inherit someone else's version of it
- You know startup pace is a real adjustment from a traditional brokerage and you want it anyway
We could treat this as maybe Skills or Qualities. But instruction only lists certain headings; we could omit this section if not matching headings. However it's substantive. Could we put under
Skills
? The list includes traits like "curious about AI tools", "want to build this function". Those could be considered skills or qualities. We'll include asSkills
with- .
Requirements list:
- 5+ years in commercial lines underwriting, account executive, wholesale brokerage, or carrier-side roles
- Active property & casualty license—we handle non-resident and reciprocal licensing across all 50 states
- Existing carrier and wholesaler relationships you can put to work
- A track record owning complex commercial cases end to end, not just triaging them
- Comfort with technology; you'll work in our service workbench daily and be expected to tell us where it falls short
- Based in New York City or San Francisco, or willing to relocate; this role is in-office
We'll put under
Requirements
as- .
Nice to Have list:
- Surplus lines license
- E&S experience: surplus lines tax, filings, binding packets, DocuSign workflows
- Premium finance depth: PFAs, reconciliation, finance-company defaults and cancellation reversals
- Workers' comp and class-code expertise, including NCCI audit disputes
- Wholesaler, MGA or carrier underwriting-desk background
- Experience at an insurtech or tech-forward brokerage
We'll put under
Qualifications
as- .
Compensation:
"Compensation Salary: $110,000–$150,000 + performance bonuses + equityLocation: San Francisco, Atlanta, or