Role Description 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. 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.

Qualifications

• 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.

Benefits

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