Chief Transformation and AI Officer
•Pentagrp· 14h
🏷️ Data Science⏰ Full-time👔 Executive💰 $450k-500k🇺🇸 USA
14h ago
Help Scout·about 17 hours ago
Help Scout builds software for relationship businesses — companies that earn loyalty through outstanding customer service. We’ve been on this journey since 2011, and today more than 10,000 companies use our platform to support 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.
The VP of Product owns business outcomes. That means the bets you make and the metrics they move, not roadmap adherence or process compliance. You set what winning looks like across all product lines, make the bets that matter most, and stay close enough to customers and data to know when to adjust and when to stop. You manage a team of PMs while staying a hands-on strategic contributor.
We have deliberately stripped out phase gates, named sign-offs, and committee reviews. Quality comes from the people doing the work and the standards senior practitioners hold, not from a review queue. Small bets ship in days, larger bets in a few weeks. We use AI tools every day for research synthesis, strategy work, customer signal analysis, and rapid prototyping. PMs at Help Scout are builders too. Using AI to fix a bug, tweak a design, or iterate on the customer experience is expected. The VP of Product shapes how the whole team uses these tools.
As we expand and diversify our suite of revenue generating products, you’ll define what winning looks like across the product suite and hold yourself accountable to it.
Make the product strategy clear and actionable for the entire org, partnering with your team, Chief Product Officer, and other senior leaders to drive prioritization across growth, intelligence, conversations, and agents capabilities.
Empower the organization to make tough tradeoffs on priority, using clear logic and guidelines.
Understand and actively manage the relationship between product decisions and business economics: pricing, packaging, retention, and margin. Product is a financial lever, not just a feature factory.
Build and develop a high-performing product team (currently 4). Set a clear outcome metric at the start of every project, then trust the team to execute.
Drive cycle times down. Eliminate gates that exist for their own sake, and build the talent density that makes trust the default.
Shape how the team uses AI, as practitioners and as product thinkers.
Spend meaningful time in customer calls, support conversations, and research. The signal you bring back is the most important qualitative input to every bet.
You proactively seek to answer complex questions by exploring data. Quantitative fluency is part of how you work, not something you delegate. You’ll leverage our data warehouse and AI-native tools including Hex, Mixpanel, and more.
You operate as a peer to cross-functional leaders, bringing product context to go-to-market, pricing, and retention decisions.
You confidently speak to Help Scout's product vision with customers and prospects. You are a credible, compelling voice for where we're going.
Develop taste and judgment within the product team through coaching, critique, and example, not through gate reviews.
You own outcomes at the business level. You measure your work by whether the bets you championed moved the metrics you predicted.
You have strong strategic judgment. You can look at a fuzzy problem space and return with a clear, prioritized set of bets. You hold strong views, defend them with evidence, and change them when the evidence demands it.
You understand what AI changes about this role. When execution is cheap, judgment is the bottleneck. You operate accordingly. You're genuinely fluent with AI tools and have a point of view on where they're taking product work.
You know the difference between being close to the work and being in the way of it. You set a clear outcome, trust the team, and resist the pull to over-specify. Your best hours go to strategy and prioritization.
You're an excellent writer and presenter. The medium of decision at Help Scout is the written word. You make your thinking visible, and you understand that good written context is how AI amplifies your strategic work.
You have strong product sense and design judgment. You notice when something is off and you hold the quality bar consistently.
You understand product as a financial lever. You connect roadmap decisions to the key financial metrics of the business.
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.
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.
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 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.
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.
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.
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.