Careers @ Headset

Founded in 2015, Headset provides industry-leading data analytics & market intelligence solutions for the emerging cannabis industry. Everything at Headset begins with retail and consumer shopping. Headset connects with point-of-sale data from retail and dispensary cooperators, giving Headset subscribers an aggregated market read, providing visibility into industry trends, market data, competitive insights and new opportunities all in real-time. We work with close to 3,500 retailers in both medical and adult-use markets in the United States and Canada, delivering comprehensive cannabis business intelligence solutions for cannabis products & businesses.
Team Headset continually striving to make cannabis company succeed by empowering them with reliable and actionable cannabis market data.
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Growth Manager, Expansion & Renewals

Your Mission:

As Headset’s Growth Manager focused on Renewals & Expansion, you will play a key role in driving revenue growth from existing customers. This role is critical to maintaining strong relationships, ensuring customer satisfaction, and identifying upsell and cross-sell opportunities across our product suite—particularly Headset Bridge, our powerful inventory & ordering platform.

What You'll Be Doing:

  • Manage and execute the renewal process for current customers to ensure retention and continuity of service.
  • Proactively identify and pursue expansion opportunities within your book of business.
  • Drive upsell and cross-sell motions across products like Headset Bridge and other market intelligence offerings.
  • Comfortable following (and improving) structured processes in a high-velocity sales environment.
  • Conduct regular business reviews with large accounts to understand their goals, challenges, and opportunities for deeper engagement.
  • Collaborate with Account Executives and the Head of Sales to develop tailored recommendations and close expansion deals.
  • Maintain a deep understanding of Headset’s products to clearly articulate value and impact.
  • Work with the Head of Sales to forecast renewals and expansion revenue with accuracy, updating CRM systems such as Salesforce and Outreach consistently.
  • Navigate complex customer orgs to uncover key stakeholders and growth opportunities.
  • Prepare and present custom proposals and negotiate contract terms that align with Headset’s business goals.
  • Support customer success and implementation teams to ensure a seamless transition from sales to post-sale engagement.
  • Willingness to travel occasionally as needed to support client relationships, growth strategy, or company events.

What Skills and Experience We Envision in the Ideal Candidate:

  • 2+ years of experience in a renewals, account management, sales, or expansion sales role.
  • Proven track record of hitting revenue targets - tied to renewals and/or expansion a plus.
  • Strong familiarity with CRM tools like Salesforce and Outreach platforms.
  • Excellent interpersonal and negotiation skills, with a strong commercial mindset.
  • Ability to build trust and communicate effectively with executive-level stakeholders.
  • Experience working in a fast-paced, high-growth, or startup environment.
  • Cannabis industry experience is a plus, but not required.
  • Highly self-motivated and proactive with a keen sense of ownership.
  • Comfortable managing multiple accounts and priorities simultaneously.
  • A team player who collaborates cross-functionally and works well independently.

Is This You?

Do you share our values? Does this sound like the kind of environment where you’ll feel inspired to do your best and most meaningful work? If the answer is yes, we’d love to hear from you.

We offer a competitive base salary, an incentive bonus for outstanding performance, a generous stock option package, and great benefits. Headset is an equal opportunity employer.

What We Believe

Our Core Values

Our mission — enable the success of the cannabis industry through unparalleled market intelligence and consumer trends, removing the guesswork from decision-making.

Ownership

We practice relentless grit: Pushing through obstacles while dedicating one’s self to take ownership of our work.

Trust

No need for silos. We let integrity guide our actions, while operating with radical transparency and trust in the people we work with.

Data

We are data driven to the core. Data drives our decision making and measurement is critical. We strive to help our customers differentiate their own success with useful data.

Growth

Rapid growth is critical to success. We employ a sense of urgency while avoiding panic. We embrace feedback with the understanding that ‘perfect is the enemy of good’.
Headset - Seattle Headquarters