Remote
SaaS
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
Typical Day — Sales Manager
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
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
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
How do you coach underperforming reps?
Template questionDescribe your forecasting methodology.
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Template questionSales 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.
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