Director, Brands & Retail Media

About the role

At Dutchie, we power the technology that helps cannabis dispensaries and brands thrive. From point of sale and payments to e-commerce and supply chain, we’re building the backbone of a modern, compliant, and customer-friendly cannabis industry.

We’re looking for a Director of Brands & Retail Media to own our Brands revenue and build toward something much larger. This is a rare role: one part commercial leader, one part entrepreneur. You’ll run a team of Account Executives and Account Managers, own the number, and simultaneously define what Dutchie’s Retail Media Network becomes — working directly with Product and Engineering to turn market insight into product bets.

The ideal candidate has led revenue teams in B2B media, retail media, or adtech, knows how to build repeatable GTM motion across a wide deal-size range, and is energized by the blank-page challenge of building a new category from a position of genuine structural advantage.

What You'll Do...

Drive Brands Revenue

• Own and grow Dutchie’s Brands revenue, with a mandate for significant scale — set commercial strategy across the full deal spectrum, from high-velocity accounts to large strategic partnerships with major cannabis brands.
• Define and track the KPIs, forecasting cadence, and operating rhythm that make this a professionally-run, predictable revenue business.

Lead and Develop the GTM Team

• Manage a team of Account Executives and Account Managers, with the expectation of growing and upgrading that team as the business scales.
• Build a best-in-class outbound hunting motion — pipeline discipline, ICP targeting, outreach sequencing, and close process.
• Build a best-in-class account management and expansion motion — QBRs, renewal playbooks, upsell identification, and churn prevention.
• Identify where inbound can supplement outbound; partner with Product Marketing to build the messaging and content engine that generates brand-side demand.

Define and Build the Retail Media Network

• Become Dutchie’s internal authority on what a Retail Media Network means in cannabis — the products, the economics, the risks, and the sequencing.
• Conduct structured discovery with brands, agencies, and platform partners to map where the highest-value unmet needs are and translate that into a clear product opportunity roadmap.
• Partner with R&D to prioritize and scope new Brands-facing capabilities; assess build vs. buy vs. partner for key capability gaps with clear risk/reward framing.
• Act as the internal voice of the brand customer, ensuring Dutchie’s platform decisions reflect what drives measurable ROI for brands.

What You Bring...

• 10+ years of experience in B2B revenue leadership, with meaningful time in retail media, digital advertising, adtech, or media networks — cannabis experience a plus but not required.
• Demonstrated track record of owning and growing a revenue number, ideally in a business that required both hunting new logos and expanding an existing customer base.
• Experience managing and developing quota-carrying sales teams; you know what good looks like and can coach to it.
• Entrepreneurial instinct — you’ve either built something from scratch or operated in an early-stage environment where you had to define the playbook, not just run it.
• Fluency in retail media network economics: how brands think about trade spend, co-op, performance marketing, and attribution; how platforms monetize audience and shelf.
• Strong product intuition — you can sit in a room with engineers and PMs, translate commercial insight into product requirements, and advocate for the right sequencing.
• Ability to operate across deal sizes and complexity, from high-velocity SMB accounts to multi-stakeholder enterprise negotiations.
• Clear, compelling communicator — written and verbal — with the executive presence to represent this business internally and externally.
• B2B SaaS or platform experience required; regulated industry experience strongly preferred.

You’ll Get…

We are targeting $230,000 – $265,000 OTE plus accelerators above quota based on the intended level for this role.

In addition to cash compensation, our total rewards package includes:

• Full medical benefits including dental and vision plans to ensure you always have the best care.
• Equity packages in the form of stock options to all employees.
• Technology (hardware, software, reading materials, etc..) allowance
• Flexible vacation and sick days