Deployment Strategist

Afresh • San Francisco, CA

5d • Remote

About The Position

As a Deployment Strategist at Afresh, you'll work with some of the largest grocers in the World to figure out where AI can make a real difference to their business — and then turn those ideas into reality. You'll sit at the intersection of strategy, customers, sales, and product, helping translate a grocer's biggest business problems into solutions that create real value. You'll work closely with our executives, commercial team, and engineers. You'll lead discovery with customers, identify and prioritize the problems worth solving, shape the opportunity, build or size the business case, and ultimately direct what we build. This is an opportunity to join a fast-growing AI company at an important moment in its evolution. You'll have the opportunity to shape how we work, what we build, and ultimately how we help define what AI looks like in the grocery industry.

Requirements

• 5+ years in a customer-facing role such as strategy or technology consulting, systems integration, solutions consulting, solutions architecture, technical pre-sales, or enterprise sales.
• Commercial instinct. You've worked closely with Sales to shape and win new business
• Strong discovery and problem-solving skills. You can get into a customer's business, ask the right questions, run effective workshops, and turn a messy business problem into a focused set of use cases and a clear path forward.
• Good judgment on what to build. You can define an MVP, establish what success looks like, make trade-offs, quantify the potential value, and build a path from the first use case to a broader solution.
• Business case development. Proven ability to develop data-driven business cases and ROI models that translate complex customer challenges into actionable solutions, securing executive buy-in and resource allocation.
• Enterprise project and stakeholder management. You've owned or played a role in complex customer engagements. Including managing the plan, scope, stakeholders, and difficult conversations.
• Executive presence. You're comfortable building relationships and driving decisions with senior executives, while also being able to get into the details with the people actually doing the work.
• Retail experience. You understand how a grocery or retail business actually operates, ideally with experience in merchandising, pricing and promotions, replenishment, supply chain, or DC and store operations.
• Technical fluency. You can have a productive conversation with engineers about data, systems, integrations, and what AI can and can't do. You are capable of explaining this clearly to a business audience without needing technical support.
• Comfort with ambiguity. You're comfortable taking on problems that don't have an obvious answer, figuring things out as you go, and moving quickly toward an outcome.
• Willingness to travel. Approximately 25–50% travel, with more travel during active deployments, and comfortable working on site with customers.
• AI fluency. You use AI tools regularly in your own work and are excited about finding practical ways to use them to work faster and better.

Nice To Haves

• Experience as an early commercial hire at a fast-growing company, helping shape what you were selling.
• Experience working on the customer side as a category manager, pricing lead, replenishment lead, DC operations manager, or planner.
• Experience with data, analytics, or AI programs at a retailer or a company selling into retail.

Responsibilities

• Find the right problems to solve. Lead discovery with merchants, planners, analysts, IT, and executives. Understand how the business works, identify the highest-value problems, and turn them into specific use cases we can solve.
• Shape the opportunity. Bring your perspective on what others are doing, what good looks like, and where the biggest opportunities are. Work with Sales to build the business case and determine what we should pursue first.
• Define the solution and guide the build. Set the MVP, success criteria, and timeline, then work closely with Engineering to make sure we're building the right thing for the customer.
• Own the customer engagement. Own the plan, stakeholders, and day-to-day rhythm from discovery through deployment. Build relationships from the people using the product to the executives making the investment, and be the person who keeps everyone moving.
• Drive adoption and expansion. Stay close after launch to make sure the solution is delivering value. Find the next opportunity, work with Sales to expand the account, and bring what you learn back to Product and Engineering.

Benefits

• Comprehensive medical, dental, and vision coverage for you and your family, with the majority of premiums covered by Afresh.
• Dedicated mental health support and counseling services.
• Competitive base salary, meaningful equity (U.S. employees), and a 401(k) program with a generous company match.
• Home office stipend and "Coworking Wallets" for flexible workspace access.
• Annual professional development budget.
• Monthly stipends for "Betterment" (wellness/lifestyle) and telecommunications.
• Flexible paid time off.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed