Director of Sales

Making videos is easy. Making them work for your business? That is where Wistia shines. Our end-to-end platform gives businesses the tools to create, host, share, and analyze videos and webinars, all in one place.

Our mission? To be the go-to video and webinar platform for businesses. And we know that mission starts with a team that feels valued, supported, and empowered to do their best work.

Why This Role Matters

Our Head of Sales will play a critical role in accelerating Wistia's revenue growth. You will build and manage a top-notch sales team, strengthen our inbound sales motion, stand up a brand-new outbound sales strategy, help us gain ground in the mid-market, and turn our comparatively new webinar product into a commercial success story. Working alongside Growth, Marketing, and Commercial Leadership, you'll sharpen our acquisition strategy and dial in the relationship between self-serve and sales ensuring the two motions compound rather than compete. You’ll also collaborate with GTM leaders to deliver a seamless customer experience and become a leading voice of the customer, shaping what we build

Who You'll Work With: You will lead a team of Account Executives and partner closely with Marketing, GTM Operations, Customer Success, Product, Finance, Growth, and our People team.

What It's Like Working on This Team: This is a hands-on, in-the-work leadership role. You will spend real time coaching reps, reviewing calls and outreach, and building the playbooks and systems that help the team perform consistently. The team values operational rigor paired with sales instinct, and collaborates closely with Marketing and GTM Operations rather than working in a silo. In addition to ensure top notch sales execution, you will also be crafting new sales strategies, as we move into the mid-market and focus on growing our webinar business.

• Why is this role exciting? You will be responsible for leading our Sales organization as we work to accelerate our revenue growth, by growing our mid-market business, gaining share in the webinar market, and launching new Creation products. You will get to build something from scratch. Our outbound motion does not exist yet, so you will design the playbook, the targeting, and the messaging, and then build the team's skills to execute it well.

• How does it directly support Wistia's mission? Wistia's mission is to be the go-to video platform for businesses, and this role directly drives the new business acquisition that fuels that growth, including helping our webinar product become a bigger part of our story.

• What interesting challenges will candidates tackle? You will uplevel our team's strategic selling skills, build outbound sales from the ground up, figure out where AI can genuinely make the team more effective, and help shape which customer segments we go after next.

Work Environment: Hybrid with In-Office Requirement: This role is based in the Boston area, with an expectation of being in our Cambridge office at least one to two days per week.

Preferred Time Zones: Eastern Time

Travel Requirements: 1-2 days/week in our Cambridge, MA office. Team and company gatherings 3-4 times per year.

Key Responsibilities

• Lead and grow a team of Account Executives selling into small and mid-market companies, coaching performance and holding a high bar.

• Develop and execute sales strategies aligned with company revenue targets and growth objectives.

• Strengthen our existing sales funnel through coaching, sharper playbooks, and operational rigor across the full sales cycle, with a particular focus on discovery and value-based selling.

• Evaluate sales performance and diagnose where the biggest opportunities / challenges are.

• Build a brand-new outbound sales strategy from the ground up: define who we target, build the playbook, and develop the team's outbound skills.

• Partner with Marketing and our Commercial Leadership Team to sharpen our acquisition strategy, including lead sources, target segments, and messaging.

• Bring AI into the sales motion in ways that make the team more effective and more efficient, from prospect research to personalized outreach.

What We're Looking For

• A proven B2B SaaS sales leader with a track record of selling to mid-market companies through both inbound and outbound motions.

• A strong coach and manager who has not just led a high-performing team, but has measurably improved one, through coaching, performance management, and the systems that make results repeatable.

• Deep fluency in value-based, strategic selling methodologies (think SPIN, Sandler, Challenger, MEDDICC), with a track record of instilling those approaches in a team.

• A customer-centric leader who genuinely understands buyers' needs and buying processes, and builds that mindset into the team's culture.

• Bonus: experience selling MarTech or a broader GTM tech stack, and experience building an outbound motion from scratch.

Why You'll Love Working at Wistia

At Wistia, we are building the leading video platform for small and medium B2B businesses, and we know that starts with our team. We support, challenge, and celebrate one another, and we invest deeply in connection. Why? Because strong relationships drive better outcomes, and because work is more meaningful when we genuinely care about the people we do it with.

We care a lot, so our benefits are actually benefits, not just the fun stuff like swag and snacks in the office (though we have lots of those too!). We know the biggest investment we can make is in our employees, so we provide:

• A competitive compensation package that includes employee stock options

• 401k with 3% company contribution, regardless of whether you contribute (Roth 401k available)

• Fully paid healthcare, dental, and vision insurance premiums (family plans included)

• Pre-tax FSA and Dependent Care Account

• 16 weeks of paid parental leave

• Flexible Time Off. Everyone should get out of their office to recharge and reboot.

• Annual professional development stipend (courses, conferences, and more)

• New hire bonus to enhance your home office setup

• Pet insurance discount

Wistia provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.