VP of Marketing

Who we are

Help Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with customers of all types, from clients to patients and beyond.

Now we’re in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world. That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it.

We’ve been a fully remote team since day one, with 120+ teammates now all over the world. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career.

If that kind of challenge gives you energy, we’d love to meet you.

This role is 100% remote and open to US-based candidates at this time.

Your Impact

Help Scout is at a pivotal moment. We’ve laid the foundation of a strong, customer-loved product with a distinct brand and a mission-driven team. Now we’re becoming an AI-driven organization with a new strategic narrative, a redefined ICP, and a go-to-market motion built to match. Our 2026 strategy is focused, ambitious, and rooted in clear outcomes, from pipeline and trials to customer expansion.

As VP of Marketing, you’ll step into a company that’s product-led, but ready to scale its reach and influence by delivering innovation to the customer support upmarket. You’ll shape not just how we grow, but how we tell our story, differentiate in a competitive space, and bring our values to life at every stage of the customer journey.

This is a rare opportunity to lead full-funnel marketing at a company that believes in craft, autonomy, and building things that matter. You won’t be fixing something broken; you’ll be building what’s next. You’ll lead three functions: Brand & Content, Performance Marketing, and Product Marketing each with a direct report owning that function, and you’ll be supported by an AEO expert and brand/paid marketing agencies.

This is a hands-on leadership role in a remote-first company. You should expect high accountability, meaningful autonomy, and the opportunity to build, test, and refine how marketing drives growth at Help Scout.

About the role

• You’ll be accountable to a marketing revenue number and KPIs, owning the engine that drives that number not just the campaigns that feed it.

• You’ll lead three teams across Brand & Content, Performance Marketing, and Product Marketing, setting a unified strategy while giving each function room to execute.

• You’ll drive Help Scout’s new strategic narrative and ICP forward, by both driving us upmarket and translating our AI-native positioning into a story the market believes and a targeting strategy that reflects who we’re built for now.

• You’ll support the full customer journey, from first touch through expansion. You see marketing as a connected journey, from brand building to customer expansion, and have driven results across that spectrum.

• You’ll bring an AI lens to everything which includes how the team uses AI to move faster and sharpen how they work, but using it to get products to market faster and market our product more intelligently.

• You’ll use data to guide decisions, challenge assumptions, and adjust strategy when the signal changes.

• You’ll establish clear planning, prioritization, and execution rhythms that provide clarity to your teams so they can operate at their best.

• You’ll be in lockstep with Product, Sales, and RevOps to shape and execute our go-to-market strategy.

• You’ll own our modern marketing systems, automation, and emerging AI tools, and ensure they’re used to drive efficiency and scale.

About You

• You’ve served as a marketing leader or Head of Growth at a B2B SaaS company in the $30M–$150M ARR range. You’ve been accountable to outcomes, not just activity, and are comfortable owning metrics that sit close to revenue.

• You’ve led marketing organizations through a narrative or repositioning shift. You know what it takes to align a team, a brand, and a go-to-market motion around a new story.

• You have a genuine point of view on how AI is changing marketing – not just as a set of tools, but as a shift in how teams operate and how products reach customers – and you’re excited to put that into practice.

• You’ve lived through moments of change that required real judgment, including pricing changes, growth plateaus, or shifts from brand-led growth to more disciplined execution.

• You hold a high bar, elevate those around you, and communicate clearly and empathetically in a remote setting.

• You like to ship, measure, adjust. You aren’t afraid of the tension between performance goals and long-term vision.

Who you’ll work with

• Andrea Kayal – you’ll report to Andrea, our CRO

• Scott Rocher – our Chief Product Officer

• Toby Gabriner – our CEO

• Great marketers like Hillary, Ty, and Abigail

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.