Pay Your Way - Credit as a Service: Head of Sales, Magento Platform

    Shop Your Way

    🇺🇸 United States
    Remote
    SaaS
    See your match score
    Posted 2 weeks ago
    Work Type

    Remote

    Vertical

    SaaS

    Source

    himalayas

    About this role

    Do you consider yourself an innovator, a builder, a game-changer? Do you have what it takes to transform the payments, loyalty, and commerce space? Do you want to help develop and scale truly “never been done before” services and technologies?

    If yes, then we want to hear from you at Shop Your Way SYW Overview Shop Your Way (“SYW”) is a high-growth FinTech and e-Commerce enablement platform that leverages a proprietary technology infrastructure to service some of the largest and most innovative brands in America.

    SYW powers multiple business and consumer services, including SYW Rewards and the SYW Mastercard, along with a leading mobile app and digital destination.

    When bundled together as part of our Pay Your Way (“PYW”) service, we have a truly differentiated loyalty + credit solution for our business partners and their customers, without the hassle of setting up a direct credit relationship with a bank or underwriter.

    This integrated module makes it easy for Partners of any size to improve their conversions, drive new revenue, save on transaction and payment costs, and create more repeat business. Today, we’re providing this “loyalty-card as a service” to Raise (gift cards) and Way (mobility) – two of the “Andreessen Horowitz Top 50 Marketplaces” – and other national brands.

    Now, we’re expanding our offering to include other new application services while also unlocking new channels. SYW is at an exciting inflection point, built for scale and driving growth.

    Key Highlights include:● Recent investment of +$30M of “growth capital” from Private Equity / Hedge Fund sponsor● Long-term strategic partnership with Citibank powering a multi-billion dollar credit portfolio● Compelling pipeline of New Business Development initiatives, focused on SYW 5321 Card Externalization (“loyalty-card as a service”)● Proprietary, best-in-class loyalty and data technology platform built to power $10+ billion of partner business● A sizable (9 million active) yet hyper local member

    Selling Motion

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Requirements at a Glance

    Bachelor's Degree·Required
    Master's/MBA·Required

    Typical Day — Sales Manager

    Executive deal support3–5/week
    Forecast & commit2×/week
    Strategic deal coaching3–5/week

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

    Role Signals

    Green Flags

    ✓
    Equity/Stock Options

    Ownership stake offered

    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

    Head-of-Sales
    Sales-Director
    Business-Development
    B2B-Sales
    E-Commerce-Sales
    —

    How do you coach underperforming reps?

    Template question
    —

    Describe your forecasting methodology.

    Template question
    —

    How do you structure onboarding for new hires?

    Template question
    Research Shop Your Way'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
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Sales leadership roles require balancing individual contributor revenue with team performance management.

    Expect to work with recurring revenue models where customer retention is as important as acquisition.

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

    Are you a closer?

    Interested in SaaS? Build your profile to get matched with roles like this.

    Explore More Sales Jobs

    Similar Roles

    Browse More Jobs

    Powered by LemClosers

    Ready to land your next closing role?

    Build your free closer profile to get matched with high-ticket sales opportunities, track applications, and showcase your track record.

    Join 500+ closers already on the platform • Free forever

    Get matched
    Create Free Profile