Help Scout

VP of Engineering

Help Scout

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

About the role

  • Your mission is to lead the world-class engineering organization (~50 people) that enables Help Scout to deliver innovative products and delight customers. You will helm our technical vision, develop our Engineering leaders, and define and execute an AI strategy that allows us to achieve ambitious product and business goals.
  • You’ll own:
  • - **Technical strategy**: Your job is to deliver a product that’s performant, secure, and reliable for customers. You'll define and execute an AI strategy that allows us to achieve an ambitious product vision centered around intelligence, while leveraging AI to unlock new capabilities across Help Scout. You’ll also be focused on code modernization efforts to ensure the team can deliver product improvements at a high velocity.
  • - **Organizational Leadership**: The organization is roughly 50 people. We have two departments: Product and Platform. Your top priority is to attract, hire, and empower the most talented engineers we can find. At Help Scout, commitment to excellence and craft is table stakes. You’ll be accountable for maintaining that standard across the board, raising that standard in critical areas for the business, and quantifying its impact on the business.
  • - **Cross-Functional Leadership**: You’ll be responsible for communicating the Engineering strategy with teammates inside and outside of the organization. It’s important that everyone knows what we’ve accomplished, how it impacts the business, and where we’re headed next. You’ll bring technical expertise to crucial business conversations at the executive level, and you’ll help our engineering teams advocate for their work across the business.
  • - **Engineering Investments**: You'll be accountable for the largest people and platform investments at Help Scout. That means owning the Engineering P&L, partnering closely with our strategic finance team to forecast and manage costs, and communicating clearly about where we're investing and why. You make smart tradeoffs and can defend them.
  • - **Roadmap execution**: Engineering, Product, and Design operate in a shared ownership model where the three disciplines make decisions together. Alongside your partners on XLT, your collective goal is to deliver great products that drive business results. Delivering a product at our scale and continuously innovating is a huge challenge. Ultimately, it's your job to show up as a partner, make clear agreements with company stakeholders, and either meet them or renegotiate them.

Requirements

  • You are an inspiring leader. You have an innate ability to paint the vision for your teams through your actions. You excel at creating alignment and fostering a culture of accountability, inclusivity, and motivation among all team members.
  • You are an engineer by trade and can operate in the details when it matters. You have a bias towards action. You've led teams before and know how to bring out their best.
  • You are a talent magnet. Great engineers love working in your organization because they have the ownership, context, and support to produce outcomes they are proud of. You lead because you love seeing others succeed and are passionate about building diverse teams that make big things happen.
  • You have a point of view on AI and you’re not afraid to experiment. You understand where it creates real leverage in engineering, and you're thoughtful about the ethical dimensions: what to automate, what to protect, and how to build systems your team trusts.
  • You are scrappy and creative. We have a small fraction of the resources our competitors have, and you see that constraint as an opportunity. With the right focus, we can move faster and out-execute the competition.
  • You are an outstanding collaborator, bridge-builder, and communicator. You leverage this skill to inform the product strategy and ensure all stakeholders feel informed and inspired by the work the team is doing.
  • You have a growth mindset. You are always asking questions, looking at data, and experimenting with new ideas that can help teams be successful. In a time of vast change and evolution, you are running at the front.
Benefits
  • Competitive salary and an internal, transparent salary formula based on market data
  • Flexible time off – you choose the holidays and vacations that make sense for you
  • 12 weeks of fully paid parental leave for all new parents, including adoption and foster care
  • A home office stipend to help you get set up and productive
  • A co-working stipend up to $300 a month if you choose to work out of your house
  • A yearly professional development stipend of $1,800 to help you grow in your craft
  • If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AI strategycode modernizationengineering leadershipproduct developmentP&L managementforecastingcost managementtechnical strategyperformance optimizationsecurity best practices
Soft Skills
inspiring leadershipalignment creationaccountabilityinclusivitymotivationcollaborationcommunicationcreativitygrowth mindsetteam empowerment