About this role.
Upside is hiring a Senior Strategic Account Executive to win and onboard enterprise fuel retailers, wholesalers, and marketers onto its commerce platform. This is a high-seniority hunter role centered on consultative, data-driven selling to director through C-suite stakeholders. The executive will own pipeline development, forecasting, opportunity management, and coordination with Sales, Product, and Marketing on launches and go-to-market strategy. Candidates need 10+ years of sales experience, including substantial enterprise SaaS, fuel, convenience retail, or downstream-energy technology exposure, and must be able to travel 30–50%. The role is location-flexible, with hybrid office attendance required for candidates based in the Washington, D.C., Austin, Chicago, or NYC metro areas.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I start by defining the ideal customer profile, mapping buying committees, and segmenting accounts by strategic fit and likelihood to buy. I combine targeted executive outreach, industry relationships, partner channels, and account-specific value hypotheses, then inspect conversion metrics weekly to improve coverage and quality.
I would first quantify the retailer’s goals around profitable traffic, loyalty, margin, and competitive differentiation. Then I would connect Upside’s measurement capabilities to a testable business case, align stakeholders on success metrics, and propose a phased launch plan that demonstrates incremental profit rather than relying on broad promotional claims.
In complex deals, I create a stakeholder map that identifies economic buyers, champions, technical evaluators, and potential blockers. I maintain a mutual action plan with clear decision criteria, tailor the value narrative to each function, and use regular executive alignment to prevent late-stage surprises.
I use objective exit criteria for every stage, document next steps and stakeholder engagement in Salesforce, and distinguish pipeline activity from verified customer intent. My forecast reviews focus on close plans, risks, decision process, and evidence of business pain so that leadership receives a realistic view of timing and probability.
I take full ownership of account strategy and commercial progress while engaging Product, Marketing, and implementation partners early when their expertise can strengthen the customer case. I provide concise context, defined asks, and shared milestones so internal teams can support the deal without losing focus on their core priorities.
Meet Upside:
We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.
The Impact You’ll Make:
Upside is a fast-growing company in search of an experienced hunter who can help drive further growth by signing up new Enterprise fuel accounts — large fuel retail chains, wholesalers, and marketers. We are looking for sellers with a consistent track record of exceeding quotas and goals. You will join a team whose experience hails from places as varied as Google, Affirm, Klarna, MasterCard, and successful startup executives and venture capitalists.
As a Senior Strategic Account Executive, Fuel, reporting to our VP, Enterprise Fuel, your responsibilities will include:
Partnering with Sales leadership and the larger fuel team to implement our sales strategy and onboard enterprise fuel accounts onto the platform
Building relationships and selling consultatively to Director, VP, and C-Level executives at enterprise fuel accounts
Effectively presenting the Upside value proposition to enterprise fuel accounts, through a data-driven, incrementality-focused sales approach
Working directly with our internal Sales, Product, and Marketing teams to support go-to-market strategy, merchant launches, roadmaps, and key partnerships
Leading and implementing effective sales strategies, pipeline management, and opportunity management
Building a pipeline and managing your forecast for new fuel merchants added to the platform
Competencies You’ll Need:
10+ years of sales experience with 7+ years of experience selling to enterprise SaaS and/or fuel, convenience retail, or downstream energy technology companies
Experience working with executives on pricing, planning, finance, and marketing is a plus
Successful track record of achieving/exceeding quotas required (existing fuel-industry relationships are a bonus, but not required)
Proven success building and scaling a book of business from early stage to high growth
Adept in structured sales training methodologies and rigorous CRM pipeline management, specifically Salesforce.
Ability to travel 30-50% of the time
Start-up experience desired
Bachelor’s degree or higher (Master’s degree preferred). Experience may be considered as a substitute for education depending on relevance
Location:
This role offers location flexibility, however, if you’re based in the Washington, D.C., Austin, Chicago, or NYC metropolitan regions, in-office attendance is required on a hybrid basis.
Compensation:
The U.S. base salary range for this full-time position is $178,000 – $200,000 + commissions + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.
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Benefits:
Medical, dental, and vision coverage starting on Day 1
Equity (ISOs)
401(k) program
Family planning programs + paid parental leave
Physical fitness and wellness memberships
Emotional and mental health support programs
Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break
Flexible work environment
Lunch reimbursement for in-office employees
Employee Resource Groups
Learning and Development stipend
Transparent culture
Amazing mission!
Diversity and Inclusion:
Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!
If there’s anything we can do to support a disability or special need during your application or interview process, please email accommodations@upside.com.
This email is for accessibility accommodations only, it should not be used to submit job applications.
Notice To Recruiters And Placement Agencies:
This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.
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