Director of Technical Success

Broccoli AI

1d•Hybrid

About The Position

About Broccoli 🥦 At Broccoli, we're building AI teammates for the people who build and maintain our world. We partner with plumbing, HVAC, and electrical contractors, the hardworking businesses that keep homes and communities running, and replace fragmented software and repetitive manual work with AI that actually gets the job done. Our AI teammates answer phones, book appointments, follow up with customers, recover missed revenue, and help contractors deliver exceptional customer experiences, all while integrating seamlessly with platforms like ServiceTitan. Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built. Today: Hundreds of contractors rely on Broccoli every day. We've grown to $15M+ ARR in under two years. We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry. We're backed by Khosla Ventures and Y Combinator. We're still just getting started. The Role We're hiring a Technical Success Director to lead and scale Broccoli's Technical Success function. Technical Success sits at the intersection of our customers, our product, and our Engineering team. As the leader of this function, you'll make sure complex customer problems don't get lost between teams. You'll build a team that can deeply understand technical issues, represent the customer's needs to Engineering, and translate technical solutions back into clear outcomes for the customer. You'll serve as the bridge between customers and Engineering, bringing customer context, business impact, and technical detail together to ensure we're solving the right problems and solving them well. At the same time, you'll build the people, processes, and systems that allow Technical Success to scale alongside Broccoli. You'll lead a highly technical team, establish how we handle support escalations, define SLAs and ticket flows, develop strong partnerships with Engineering and Product, and continuously turn what we learn from customers into better products and better experiences. This is a hands-on leadership role for someone who enjoys solving complex problems, developing people, building systems, and operating at the intersection of customer experience and technology.

Requirements

8-12+ years of experience in technical support, technical account management, solutions engineering, implementation, customer success, or a similar customer-facing technical role
4+ years leading and developing technical teams, including experience building or materially redesigning a support or technical-success operating model
Experience supporting a mission-critical, integration-heavy SaaS product where customer issues may require rapid coordination across Support, Engineering, and Product
Demonstrated experience establishing escalation frameworks, SLAs, ticket routing, quality programs, incident processes, and durable Engineering and Product feedback loops
Experience partnering with Engineering and Product to investigate customer-impacting issues, translate technical complexity clearly, and drive resolution.
Strong ability to translate between technical and non-technical audiences and communicate complex problems clearly
Experience partnering closely with Engineering or Product to investigate and resolve customer-impacting issues
Excellent judgment and ownership when navigating ambiguous, high-impact, or time-sensitive problems
A track record of building or improving processes, systems, and teams in a fast-moving environment
A customer-first mindset with the ability to balance speed, quality, and technical rigor
Comfortable operating at both the strategic and tactical level—you can build the strategy while still jumping into a difficult escalation when needed

Nice To Haves

Experience leading Technical Success, Technical Support, Support Engineering, Technical Account Management, or a similar function in a startup environment
Experience with AI, conversational AI, voice, communications, or workflow automation products
Experience supporting integrations with platforms such as ServiceTitan, CRMs, ticketing systems, or other business-critical software
Experience supporting mid-market or enterprise customers
Experience working in a high-growth startup environment
Experience influencing Product and Engineering roadmaps through customer feedback and technical insights

Responsibilities

Lead, coach, and develop the AI Tech Support team, creating a culture of ownership, technical excellence, and customer obsession
Set clear expectations, goals, and performance standards for the team
Hire and scale the team as Broccoli's customer base and technical needs grow
Develop technical expertise across the team through coaching, training, documentation, and hands-on problem solving
Create an environment where team members are empowered to investigate problems, make decisions, and own issues through resolution
Maintain a strong partnership between Technical Success and Customer Success
Maintain a high bar for both technical quality and customer experience
Serve as the primary bridge between customer-facing teams and Engineering for complex technical issues
Ensure customer problems are deeply understood, accurately diagnosed, and translated into clear, actionable solutions
Bring the customer's business context, impact, urgency, and desired outcome to Engineering, not just the symptoms of a technical issue
Partner with Engineering to triage, investigate, prioritize, and resolve customer-impacting issues
Establish clear escalation standards so Engineering receives high-quality, actionable issues rather than incomplete or ambiguous escalations
Represent the customer's perspective in technical discussions while translating technical complexity back into clear answers for customers and Customer Success
Own the communication loop throughout an escalation, ensuring customers and internal teams always understand what is happening, what is known, and what comes next
Identify patterns across customer issues and partner with Engineering and Product to address root causes rather than repeatedly solving the same problem
Build trust between Technical Success and Engineering so both teams see each other as partners in solving customer problems
Define and execute the strategy, priorities, and operating model for Technical Success
Establish scalable processes for technical support, troubleshooting, escalation, incident management, and issue resolution
Develop and monitor key metrics around response times, resolution times, quality, customer impact, escalations, and team performance
Build the documentation, troubleshooting guides, playbooks, and internal resources needed to scale technical expertise
Identify opportunities to automate, simplify, or eliminate repetitive technical work
Establish processes that turn customer issues and technical learnings into improvements across Product, Engineering, and Customer Success
Continuously evaluate how Technical Success should evolve as Broccoli's product, technology, and customer base grow