--- title: 'Head of Solutions at Pylon' canonical: 'https://feeny.ai/job/head-of-solutions-pylon-san-francisco-36ghtxzy6e0s' type: 'job' last_seen: '2026-10-15' --- # Head of Solutions at Pylon - **Company:** Pylon - **Location:** San Francisco, CA - **Employment:** full-time - **Posted:** 2026-06-08 - **Last confirmed live:** 2026-10-15 - **Apply:** https://jobs.ashbyhq.com/pylon-labs/db624284-3e08-4681-ac39-864cee5e475f ## Job description 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](http://Incident.io) run their support and customer success workflows on Pylon. We're also featured on the [Enterprise Tech 30 List](https://www.enterprisetech30.com/). Company - Series B, $51M raised - Backed by a16z, BCV, General Catalyst, Y Combinator - 100+ employees - Offices in San Francisco and NYC (London coming soon!) ## The Role We’re hiring our first dedicated Solutions leader. This person will own the technical customer journey end-to-end: from pre-sales solution design to implementation, deployment, and long-term customer success. You’ll build the function, define the playbooks, and set the standard for how technical customer-facing work gets done at our company. This is a player-coach role. We’re looking for someone who can personally lead strategic deployments, run complex customer engagements, and build the systems, processes, and team that allow us to scale. ## What You’ll Do Build the Solutions Function - Define and own the operating model for Solutions. - Build the playbooks, processes, and tooling that allow us to scale customer deployments. - Establish clear ownership and interfaces across Sales Engineering, Implementation, Forward Deployed Engineering, and Professional Services. - Create repeatable systems that reduce deployment time while improving customer outcomes. Set the Standard - Personally lead high-impact customer engagements, implementations, and technical escalations. - Establish the gold standard for customer communication, project management, and technical execution. - Turn your own best practices into repeatable playbooks for the team. - Be the leader who can jump into any customer situation and help move it forward. Build and Lead the Team - Recruit, hire, and develop world-class Solutions talent. - Coach Sales Engineers, Implementation Engineers, and Forward Deployed/Solutions Engineers. - Create clear career paths and performance expectations across the function. - Scale the organization without sacrificing quality. Be the Bridge Across the Company - Partner closely with Sales, Product, Engineering, and Customer Success. - Bring customer feedback directly into product and engineering discussions. - Help shape how the company approaches deployments, integrations, and technical partnerships. - Act as the connective tissue between customers and internal teams. ## What You’ve Done - Built or scaled a Solutions, Solutions Engineering, Implementation, Customer Engineering, or Professional Services function at a B2B software company. - Personally ran demos, implementations, integrations, migrations, or deployments before becoming a manager. - Hired and developed customer-facing technical talent rather than inheriting an existing organization. - Built processes and playbooks that allowed a team to scale. - Thrived in ambiguous environments where the right answer did not already exist. This Role Might Not Be For You If - You want to manage people more than you want to do the work. - You prefer operating within established processes rather than creating them. - You are looking for a narrowly defined function with clear boundaries. - You want to apply the same playbook you’ve used before without adapting it to a new category. - You prefer remote or hybrid work. This role is based in San Francisco alongside the rest of the Solutions team. Our perks 🚆 Commuter benefits 🌱 Parental leave 🏝️ 14 company holidays + unlimited PTO 🗺️ Annual offsite 🍽 Lunch, dinner, and snacks at the office 🏋️ Fitness stipend More about Pylon Funding: Series B led by a16z and BCV ($51M total raised) Founders: [Advith Chelikani](https://www.linkedin.com/in/advith/), [Robert Eng](https://www.linkedin.com/in/robert-eng/), and [Marty Kausas](https://www.linkedin.com/in/martykausas) Team: Currently 100+ and growing! ## About Pylon ## Company Overview - **One-liner**: Pylon is an AI-native customer support platform purpose-built for B2B companies, unifying conversations across Slack, Teams, email, and chat into a single intelligent workspace. - **Entity Type**: Private (Series B – $31M raised August 2025, total funding ~$51.3M) - **Headquarters**: San Francisco, California, USA - **Founded**: 2022 (Y Combinator Winter 2023 batch) - **Founders**: Advith Chelikani (Co-Founder & CEO), Robert Eng (Co-Founder), Marty Kausas (Co-Founder) ## Core Business - **Primary industry**: Customer Support / Customer Service Software (SaaS) - **Target customers**: B2B companies of all sizes, from startups (e.g., Vellum, Hightouch, Deel) to mid-market and enterprise. - **Mission / purpose**: To build the first customer support platform designed for how B2B teams actually work – with complex accounts, multiple stakeholders, and conversations across many platforms. ## Products & Services - **Omnichannel Support**: A single view for all customer conversations across Slack Connect, Microsoft Teams, Discord, email, in-app chat, WhatsApp, and ticket forms. Manages both internal and external channels. - **AI Assistants + Agents**: AI-powered tools that automatically route issues based on intent, draft replies and knowledge articles, categorize tickets, surface account insights, generate charts, and answer natural-language questions about customers. Can resolve 50% of eligible inquiries without human intervention. - **Knowledge Automation**: AI that identifies gaps in the knowledge base, drafts articles, and surfaces the right answers before the support team has to search. - **Account Intelligence**: Automatically tracks churn signals, feature requests, renewal risk, and other key account data, surfacing full customer context in seconds for support, success, and sales teams. ## Market Standing - **Valuation / Market Cap**: Not publicly disclosed - **Key Metric**: Total funding of **$51.3M** (Pre-Seed $125K from Y Combinator, Seed $3.2M led by General Catalyst, Series A $17M led by a16z, Series B $31M led by Bain Capital Ventures and a16z). Estimated annual revenue of **~$2.3M** as of mid-2025 (LinkedIn estimate). - **Notable Investors / Partners**: Andreessen Horowitz (a16z), Bain Capital Ventures, General Catalyst, Y Combinator. - **Growth Signals**: - Headcount grew **158% YoY** to ~87 employees (July 2025). - Claims **90% decrease in First Response Time** (from 35 minutes to <3.5 minutes) and **8x faster resolution time** despite 76% more ticket volume. - Customers include YC companies like Vellum, Hightouch, and Deel. - 50% of eligible inquiries resolved without human intervention. - Active hiring across engineering, customer success, sales, product, and GTM roles. ## Competitive Advantages - **AI-native architecture**: Built from the ground up with AI, rather than bolting AI onto legacy platforms like Zendesk or Intercom. - **B2B-specific channel support**: First platform to natively integrate Slack Connect, Microsoft Teams, and community channels (Discord) – critical for B2B workflows. - **Account Intelligence**: Proactive detection of churn risk, feature requests, and renewal signals from support conversations, shared across support, success, and sales. - **Compliance & security**: SOC 2 Type II, GDPR, ISO 27001, and HIPAA compliant, making it suitable for regulated industries. ## Strategic Focus - **Current priorities**: Deepening AI automation (agents, knowledge base, routing), expanding omnichannel integrations, and scaling the go-to-market organization to capture more mid-market and enterprise customers migrating off legacy tools (e.g., Zendesk, Intercom, Freshdesk, Salesforce Service Cloud). - **Direction for growth**: Become the default support platform for all B2B companies, leveraging AI to handle routine issues while empowering agents with full context. ## Why Work Here - **Culture highlights**: Mission-driven team building the “first B2B support platform,” with a strong engineering background (founders from Caltech, Airbnb, Samsara, Affinity). Fast-paced startup environment. - **Remote/hybrid policy**: In-person at the San Francisco office. - **Notable perks/engineering culture**: Cutting-edge AI work; chance to shape product from early stage; exposure to founders and experienced leaders (e.g., Head of Engineering from Samsara). High growth means opportunity for impact and career acceleration. ## Sources 1. [usepylon.com](https://www.usepylon.com/) 2. [Pylon Jobs (Ashby)](https://jobs.ashbyhq.com/pylon-labs) 3. [Y Combinator – Pylon](https://www.ycombinator.com/companies/pylon-2) 4. [LinkedIn – Pylon](https://www.linkedin.com/company/usepylon) ## Other roles at Pylon - [Product Designer](https://feeny.ai/job/product-designer-pylon-san-francisco-8eccmp19j35t) — San Francisco, CA - [Head of Customer Success](https://feeny.ai/job/head-of-customer-success-pylon-san-francisco-rbrzwr2v0z9n) — San Francisco, CA - [Financial Controller](https://feeny.ai/job/financial-controller-pylon-san-francisco-snfmn7m5fana) — San Francisco, CA - [Software Engineer, Intern](https://feeny.ai/job/software-engineer-intern-pylon-san-francisco-arbcpptxzwx7) — San Francisco, CA - [Software Engineer, AI](https://feeny.ai/job/software-engineer-ai-pylon-san-francisco-wn7yjd0aadyt) — San Francisco, CA - [Software Engineer, New Grad](https://feeny.ai/job/software-engineer-new-grad-pylon-san-francisco-qj78fzaa0rv4) — San Francisco, CA - [Software Engineer, Security](https://feeny.ai/job/software-engineer-security-pylon-san-francisco-ysnmbrj39pzz) — San Francisco, CA - [Software Engineer, Infrastructure](https://feeny.ai/job/software-engineer-infrastructure-pylon-san-francisco-ytb536zjw32v) — San Francisco, CA - [Software Engineer, Product](https://feeny.ai/job/software-engineer-product-pylon-san-francisco-773cqvajaaxq) — San Francisco, CA - [Head of Support](https://feeny.ai/job/head-of-support-pylon-san-francisco-bvkcvmnhgjjs) — San Francisco, CA