Upside logo

    Senior Strategic Account Executive

    Upside

    🇺🇸 USA
    Remote
    ["Full-Time"]
    SaaS
    Base + Commission
    See your match score
    Posted 3 weeks ago
    Job Type

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobicy

    About this role

    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 fo

    Selling Motion

    Sales Cycle

    Enterprise

    6–18 month cycles, complex multi-stakeholder deals

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Territory

    Named Accounts

    Pre-assigned list of target companies

    Requirements at a Glance

    Bachelor's Degree·Required
    Master's/MBA·Required
    Pipeline Management·Required skill
    C-Suite Selling·Required skill

    Typical Day — Account Executive

    Stakeholder meetings3–5/week
    Executive presentations2–3/week
    Business cases & RFPs1–2/week
    Forecast & pipeline2×/week
    Champion coachingDaily

    Estimates based on role type and selling motion — actual may vary by company.

    SaaS — Interview Intel

    Typical Sales Cycle

    30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)

    Common Buyer Objections

    • "We're locked into a contract with [competitor]"
    • "We built something in-house already"
    • "We don't have budget until next quarter"
    • "Our team won't adopt another tool"

    Key Industry Metrics

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    Hot Topics to Reference

    • • AI-native product disruption
    • • PLG vs sales-led motion debate
    • • Vertical SaaS consolidation
    • • Usage-based pricing models

    Use these insights to speak the buyer's language in interviews.

    Tags

    partnerships
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research Upside's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Research typical OTE splits for this role level and negotiate accordingly
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Account Executives are the revenue engine of any sales organization — this role will require strong pipeline management and closing skills.

    Top SaaS reps often earn significant upside through accelerators once quota is exceeded.

    This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.

    Are you a closer?

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