Head of Customer Success
Pylon · San Francisco, CA · 1 mo ago
On-siteOTHRFull-time
We need to output HTML fragment with sections: About the role, Responsibilities (What You'll Do), Requirements/Qualifications (What Makes You a Great Fit, What You'll Bring), Benefits (OUR PERKS). Possibly Pay and Schedule not present, so omit. Use for each section heading. Use
for each section heading. Use - for lists. Use
for prose. Remove boilerplate. Ensure we preserve all substantive info.
We need to parse the posting.
First, there is introductory paragraph about Pylon. That is likely part of "About the role"? Actually "About The Role" heading appears later. The intro before that is company description. Should we include that? The instruction: "use
for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." The page already shows job title; we should not repeat job title as heading. The intro about company could be part of "About the role" or maybe a separate "About the company"? Not listed. Probably we should include it under "About the role" as description. The heading "About The Role" appears; we should use that as heading.
Thus structure:
About the role
... company description + role summary ...
Then responsibilities: "What You'll Do" with bullet points.
Then requirements/qualifications: combine "What Makes You a Great Fit" and "What You'll Bring". Could be separate sections: Requirements and Qualifications. But we can combine into one "Requirements" or separate. The instruction: prefer few substantive sections over many thin ones. So maybe one "Requirements" section covering both.
Then benefits: "OUR PERKS" as Benefits.
We must not include Pay or Schedule sections.
We need to preserve all substantive info: list items etc.
Let's extract.
Company description intro:
"Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work, investigating, resolving, and acting on every signal across every channel that matters. Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself. We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List."
Then "About The Role" heading and paragraph:
"Pylon is looking for a Head of Customer Success to own how post-sales works at Pylon, and to scale it, not rebuild it. You'll inherit a Customer Success organization that works: 159% NRR, quarterly expansion goals at scale, and a 15+ person team across SF, NYC, and London with team leads already in place. The systems run. Your job is to scale the team, from team leads to a management layer, and from strong quarters to a durable machine, all while leading Pylon's biggest bet: making agentic support the way our 1,600+ customers work. This is one of the most strategic seats we'll fill this year. Our customers are support and CS leaders themselves, so they look to us for how other companies use Pylon to run support and success, and how we do it internally. You'll sit at the forefront of the next generation of CS, with real room to become a thought leader in the community."
Then "What You'll Do" with bullet points:
- Own the Number: Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board. Own the expansion number. Cross-sell and upsell are not handed off to someone else, they're a core part of how you run the org, and you're directly accountable for hitting the quarterly expansion goal. Run the commercial system: quarterly goal setting (bottoms-up and top-down), pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design tied to the company's bets.
- Lead the Agentic Motion: Drive Agentic Support deployment and usage across the customer base, the company's top priority, run through your team. Own the customer migration motion to agentic, usage-based billing: drive adoption of the usage-based product, guide customers through the transition, and land successful migrations. This isn't ownership of pricing strategy itself, it's ownership of how customers actually get there. Have a strong point of view on how AI changes the customer success role, and be able to implement that transformation internally as well as help carry it through to our product.
- Scale the Org: Grow the team across three offices: hire and develop managers (two team leads are already ready for that step), own segment design across Enterprise, Mid-Market, and Scaled, book economics, and capacity planning. Own the Sales to CS relationship: qualification criteria, deal review, and customer expectations post sales. Run CS as Customer Zero: Lead the dogfooding and Championship programs, where CSM DRIs master a Pylon workflow with the PM and champion it to the team. Use Pylon every day for your own workflows. Your hands-on usage directly shapes what we build next.
- Be Pylon's Voice in the CS Community: Represent Pylon externally through speaking, writing, podcasts, and the communities where support leaders compare notes. The person who runs CS at Pylon should be a name our buyers know.
Then "What Makes You a Great Fit" paragraph with bullet-like sentences:
- You move fluidly between altitudes: building the board deck in the morning, hopping on an escalation call to save a renewal in the afternoon, and hosting a CS leader dinner in the evening. Equally strategic and hands on.
- You've owned the number, not just the relationship. NRR, GRR, expansion targets: personally accountable, at scale, with a track record of hitting them.
- You've led leaders. You get as much energy developing a manager as closing a deal, and you know the difference between running 50 people and running 50 people well.
- You inherit well. You get energy from scaling systems that already work, and you earn the right to change them by understanding them first.
- A 1,600+ account base energizes you. Our customers range from four figures to six figures, and we're building a CS org to support all of them.
- You want the stage. You already speak, write, or build in public about how customer success should work, or you've been waiting for the company and platform that makes it worth doing.
- You're AI native. You use agents in your own workflow, you can demo ours credibly to a skeptical CCO, and you have a real point of view on what agentic CS looks like.
Then "What You'll Bring":
- Experience leading customer success at a company with an agentic and/or usage-based billing product. You've lived through this exact shift before, helping customers understand variable consumption and tying value to real-time usage. This matters more to us than almost anything else on this list.
- 5+ years in post-sales, with 2+ years leading customer success organizations, including managing managers in an org of 15+ people across segments and geographies.
- A track record of personally owning and exceeding NRR and expansion targets in B2B SaaS.
- Experience scaling a CS org through an inflection point: hypergrowth, multi-geo expansion, or a pricing model shift.
- Based in San Francisco or willing to relocate, with real enthusiasm for working in person.
- Nice to have: an existing public presence in the CS community (speaking, writing, or communities like Support Driven), and EMEA team experience.
Then "WHY THIS ROLE" maybe not needed as separate section; could be part of About the role? But we can incorporate into About the role or maybe a separate "Why this role" but not in list of headings. Probably we can omit or incorporate into About the role. The instruction: include a section ONLY when the posting has real, specific content for it. The "WHY THIS ROLE" is a heading but we could treat it as part of About the role or maybe as a separate section "Why this role". However the allowed headings list does not include "Why this role". So better to incorporate that content into About the role or maybe into Benefits? It's more about role. Let's incorporate into About the role after the initial description.
Then "OUR PERKS" list:
- Fully covered medical, dental, and vision insurance for employees
- 401(k) retirement plan
- Commuter benefits
- Parental leave
- 14 company holidays + unlimited PTO
- Annual offsite
- Lunch, dinner, and snacks at the office
- Fitness stipend
We need to output HTML fragment.
We'll structure:
About the role
... company description + role summary + why this role ...
Responsibilities
- Own the Number: ...
- Lead the Agentic Motion: ...
- Scale the Org: ...
- Be Pylon's Voice in the CS Community: ...
Requirements
- What Makes You a Great Fit: ... maybe we need to break into bullet points? Could combine into a paragraph? But we need to use
- for any list of duties/requirements/benefits. The "What Makes You a Great Fit" is a list of traits; we can make each bullet a
- . Similarly "What You'll Bring" is list of qualifications. Could combine both under Requirements with subheadings? But we cannot add extra headings besides allowed ones. Could we have two sections: Requirements and Qualifications? That would be more sections but still okay if they have substantive content. The instruction: prefer a few substantive sections over many thin ones. Having two sections (Requirements and Qualifications) might be okay. But we could also merge into one Requirements section with combined bullets. However the content is distinct: "What Makes You a Great Fit" are more about traits, "What You'll Bring" are experience/requirements. Might be better to split into Requirements and Qualifications.
Let's do:
Requirements
- What Makes You a Great Fit: ... (maybe we need to break into multiple
- items)
But that would be weird: a single - containing a paragraph. Better to split each bullet as its own
- . So we need to parse each bullet point.
Let's extract each bullet from "What Makes You a Great Fit":
1. You move fluidly between altitudes: building the board deck in the morning, hopping on an escalation call to save a renewal in the afternoon, and hosting a CS leader dinner in the evening. Equally strategic and hands on.
2. You've owned the number, not just the relationship. NRR, GRR, expansion targets: personally accountable, at scale, with a track record of hitting them.
3. You've led leaders. You get as much energy developing a manager as closing a deal, and you know the difference between running 50 people and running 50 people well.
4. You inherit well. You get energy from scaling systems that already work, and you earn the right to change them by understanding them first.
5. A 1,600+ account base energizes you. Our customers range from four figures to six figures, and we're building a CS org to support all of them.
6. You want the stage. You already speak, write, or build in public about how customer success should work, or you've been waiting for the company and platform that makes it worth doing.
7. You're AI native. You use agents in your own workflow, you can demo ours credibly to a skeptical CCO, and you
for prose. Remove boilerplate. Ensure we preserve all substantive info. We need to parse the posting. First, there is introductory paragraph about Pylon. That is likely part of "About the role"? Actually "About The Role" heading appears later. The intro before that is company description. Should we include that? The instruction: "use
for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." The page already shows job title; we should not repeat job title as heading. The intro about company could be part of "About the role" or maybe a separate "About the company"? Not listed. Probably we should include it under "About the role" as description. The heading "About The Role" appears; we should use that as heading.
Thus structure:
About the role
... company description + role summary ...
Then responsibilities: "What You'll Do" with bullet points. Then requirements/qualifications: combine "What Makes You a Great Fit" and "What You'll Bring". Could be separate sections: Requirements and Qualifications. But we can combine into one "Requirements" or separate. The instruction: prefer few substantive sections over many thin ones. So maybe one "Requirements" section covering both. Then benefits: "OUR PERKS" as Benefits. We must not include Pay or Schedule sections. We need to preserve all substantive info: list items etc. Let's extract. Company description intro: "Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work, investigating, resolving, and acting on every signal across every channel that matters. Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself. We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List." Then "About The Role" heading and paragraph: "Pylon is looking for a Head of Customer Success to own how post-sales works at Pylon, and to scale it, not rebuild it. You'll inherit a Customer Success organization that works: 159% NRR, quarterly expansion goals at scale, and a 15+ person team across SF, NYC, and London with team leads already in place. The systems run. Your job is to scale the team, from team leads to a management layer, and from strong quarters to a durable machine, all while leading Pylon's biggest bet: making agentic support the way our 1,600+ customers work. This is one of the most strategic seats we'll fill this year. Our customers are support and CS leaders themselves, so they look to us for how other companies use Pylon to run support and success, and how we do it internally. You'll sit at the forefront of the next generation of CS, with real room to become a thought leader in the community." Then "What You'll Do" with bullet points: - Own the Number: Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board. Own the expansion number. Cross-sell and upsell are not handed off to someone else, they're a core part of how you run the org, and you're directly accountable for hitting the quarterly expansion goal. Run the commercial system: quarterly goal setting (bottoms-up and top-down), pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design tied to the company's bets. - Lead the Agentic Motion: Drive Agentic Support deployment and usage across the customer base, the company's top priority, run through your team. Own the customer migration motion to agentic, usage-based billing: drive adoption of the usage-based product, guide customers through the transition, and land successful migrations. This isn't ownership of pricing strategy itself, it's ownership of how customers actually get there. Have a strong point of view on how AI changes the customer success role, and be able to implement that transformation internally as well as help carry it through to our product. - Scale the Org: Grow the team across three offices: hire and develop managers (two team leads are already ready for that step), own segment design across Enterprise, Mid-Market, and Scaled, book economics, and capacity planning. Own the Sales to CS relationship: qualification criteria, deal review, and customer expectations post sales. Run CS as Customer Zero: Lead the dogfooding and Championship programs, where CSM DRIs master a Pylon workflow with the PM and champion it to the team. Use Pylon every day for your own workflows. Your hands-on usage directly shapes what we build next. - Be Pylon's Voice in the CS Community: Represent Pylon externally through speaking, writing, podcasts, and the communities where support leaders compare notes. The person who runs CS at Pylon should be a name our buyers know. Then "What Makes You a Great Fit" paragraph with bullet-like sentences: - You move fluidly between altitudes: building the board deck in the morning, hopping on an escalation call to save a renewal in the afternoon, and hosting a CS leader dinner in the evening. Equally strategic and hands on. - You've owned the number, not just the relationship. NRR, GRR, expansion targets: personally accountable, at scale, with a track record of hitting them. - You've led leaders. You get as much energy developing a manager as closing a deal, and you know the difference between running 50 people and running 50 people well. - You inherit well. You get energy from scaling systems that already work, and you earn the right to change them by understanding them first. - A 1,600+ account base energizes you. Our customers range from four figures to six figures, and we're building a CS org to support all of them. - You want the stage. You already speak, write, or build in public about how customer success should work, or you've been waiting for the company and platform that makes it worth doing. - You're AI native. You use agents in your own workflow, you can demo ours credibly to a skeptical CCO, and you have a real point of view on what agentic CS looks like. Then "What You'll Bring": - Experience leading customer success at a company with an agentic and/or usage-based billing product. You've lived through this exact shift before, helping customers understand variable consumption and tying value to real-time usage. This matters more to us than almost anything else on this list. - 5+ years in post-sales, with 2+ years leading customer success organizations, including managing managers in an org of 15+ people across segments and geographies. - A track record of personally owning and exceeding NRR and expansion targets in B2B SaaS. - Experience scaling a CS org through an inflection point: hypergrowth, multi-geo expansion, or a pricing model shift. - Based in San Francisco or willing to relocate, with real enthusiasm for working in person. - Nice to have: an existing public presence in the CS community (speaking, writing, or communities like Support Driven), and EMEA team experience. Then "WHY THIS ROLE" maybe not needed as separate section; could be part of About the role? But we can incorporate into About the role or maybe a separate "Why this role" but not in list of headings. Probably we can omit or incorporate into About the role. The instruction: include a section ONLY when the posting has real, specific content for it. The "WHY THIS ROLE" is a heading but we could treat it as part of About the role or maybe as a separate section "Why this role". However the allowed headings list does not include "Why this role". So better to incorporate that content into About the role or maybe into Benefits? It's more about role. Let's incorporate into About the role after the initial description. Then "OUR PERKS" list: - Fully covered medical, dental, and vision insurance for employees - 401(k) retirement plan - Commuter benefits - Parental leave - 14 company holidays + unlimited PTO - Annual offsite - Lunch, dinner, and snacks at the office - Fitness stipend We need to output HTML fragment. We'll structure:About the role
... company description + role summary + why this role ...
Responsibilities
- Own the Number: ...
- Lead the Agentic Motion: ...
- Scale the Org: ...
- Be Pylon's Voice in the CS Community: ...
Requirements
- What Makes You a Great Fit: ... maybe we need to break into bullet points? Could combine into a paragraph? But we need to use
- for any list of duties/requirements/benefits. The "What Makes You a Great Fit" is a list of traits; we can make each bullet a
- . Similarly "What You'll Bring" is list of qualifications. Could combine both under Requirements with subheadings? But we cannot add extra headings besides allowed ones. Could we have two sections: Requirements and Qualifications? That would be more sections but still okay if they have substantive content. The instruction: prefer a few substantive sections over many thin ones. Having two sections (Requirements and Qualifications) might be okay. But we could also merge into one Requirements section with combined bullets. However the content is distinct: "What Makes You a Great Fit" are more about traits, "What You'll Bring" are experience/requirements. Might be better to split into Requirements and Qualifications.
Let's do:
Requirements
- What Makes You a Great Fit: ... (maybe we need to break into multiple
- items)
- containing a paragraph. Better to split each bullet as its own
- . So we need to parse each bullet point. Let's extract each bullet from "What Makes You a Great Fit": 1. You move fluidly between altitudes: building the board deck in the morning, hopping on an escalation call to save a renewal in the afternoon, and hosting a CS leader dinner in the evening. Equally strategic and hands on. 2. You've owned the number, not just the relationship. NRR, GRR, expansion targets: personally accountable, at scale, with a track record of hitting them. 3. You've led leaders. You get as much energy developing a manager as closing a deal, and you know the difference between running 50 people and running 50 people well. 4. You inherit well. You get energy from scaling systems that already work, and you earn the right to change them by understanding them first. 5. A 1,600+ account base energizes you. Our customers range from four figures to six figures, and we're building a CS org to support all of them. 6. You want the stage. You already speak, write, or build in public about how customer success should work, or you've been waiting for the company and platform that makes it worth doing. 7. You're AI native. You use agents in your own workflow, you can demo ours credibly to a skeptical CCO, and you