VP of Engineering

Who we are

At Help Scout, we’re on a mission to help businesses delight more customers. We’ve been on this journey since 2011, and today more than 10,000 companies use our platform to provide outstanding customer support. We’ve been fully remote from the beginning, and have a team of 130+ people all over the world.

We love crafting beautiful products and growing a business together, but we're also trying to do something bigger. We're building a company that brings out your best and leaves the world a better place — a company that seeks balance between profit and purpose. That's why we've been a Certified B Corporation since 2019 and have pledged 1% of our equity back to the community.

Help Scout’s success hinges on hiring talented, high-accountability people who want to be part of creating a culture where we all feel challenged and supported to do our best work. We hope that excites you to join us! 

Impact

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.

About the role

This role reports to Chief Product Officer, Scott Rocher. You’ll be part of two leadership teams at Help Scout: SLT (Senior Leadership Team) and XLT (Experience Leadership Team). The latter includes leaders from Product, Engineering, and Design. We’ll all be working together to craft a product people love.

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.

About you

• 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.

The team also made a deck for this role that you can check out here.

Company values

Happy to Help

Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community.

Craft over Convention

Our success relies on the quality and craft of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

Progress not Perfection

Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better.

Own the Outcome

Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along.

Read more about how we define, share, and live these values here.

Benefits And Perks

• 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.

Hiring Guidelines:

All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements.

We do not sponsor visas. Teammates must already be authorized to work from their home country.

We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it's the right thing to do.

To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them.

A note on the use of AI in our interview process

While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we'd like for you to have a real human-to-human conversation with our team.

On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.