Director of Sales

About the role

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.

This role is a hands-on, in-the-work leadership position. 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 ensuring 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.

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.

This role directly supports Wistia's mission to be the go-to video platform for businesses by driving new business acquisition that fuels growth, including helping our webinar product become a bigger part of our story.

You will tackle challenges such as upleveling our team's strategic selling skills, building outbound sales from the ground up, figuring out where AI can genuinely make the team more effective, and helping shape which customer segments we go after next.

Work Environment

This is a hybrid role based in the Boston area, with an expectation of being in our Cambridge office at least one to two days per week. Travel requirements include 1-2 days per week in our Cambridge, MA office, along with team and company gatherings 3-4 times per year.

Responsibilities

• Lead and grow a team of Account Executives and BDRs 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 and 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 efficient, from prospect research to personalized outreach.

Requirements

• 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 systems that make results repeatable.
• Deep fluency in value-based, strategic selling methodologies (e.g., 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.

Benefits

• 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.