Role Description We're hiring a Customer Success Manager to own our brand relationships from the first day of onboarding through renewal and expansion. You'll be the person brands trust to make Checkmate work for them: live fast, revenue early, and strong first results that turn into long-term partnerships. This is a high-ownership role on a small team. You'll carry your own book of brands, run those relationships end to end, and sit close to the revenue we deliver. If you like owning outcomes, moving fast, and being the reason a brand stays and grows, you'll thrive here. What You’ll Do - Onboarding & Activation - Lead onboarding for new brands, from kickoff through go-live - Configure each brand's offers, channels, and audiences for their goals - Set success metrics and a clear first-30-days plan with every brand - Get brands to first revenue quickly and cleanly - Account Management - Own a book of brands as their main point of contact - Run regular check-ins, business reviews, and performance recaps - Track account health, usage, and renewal timelines - Get ahead of risk before it reaches a renewal - Retention & Growth - Own renewals across your book - Identify expansion opportunities and build the case with data - Turn strong results into case studies and references - Cross-Functional Execution - Work with Rev Ops to translate performance into account actions - Bring brand feedback to Product and Ops, and flag what matters - Partner with Sales on clean handoffs and account planning - Build for Scale - Help standardize onboarding playbooks and account templates - Improve CS workflows and reduce manual steps - Contribute to repeatable processes as the team grows Who You Are - You build trust fast, and people want to keep working with you - You're energized by ownership and comfortable being the single point of accountability for an account - You read the data, find the story in it, and turn it into a recommendation a brand will act on - You stay organized and move fast when you're juggling a lot at once - You're genuinely curious about ecommerce and what makes brands grow What You Bring - 3+ years in customer success, account management, or partnerships, ideally in martech, ecommerce, or SaaS - A track record of retaining and growing a book of business - Comfort with performance data and the ability to turn metrics into a clear narrative - Sharp communication, whether you're running a business review or writing a follow-up - Bonus: you already know the DTC stack (Klaviyo, Attentive, Shopify) or have worked with DTC brands Why Join Checkmate - Solve real problems: Help DTC brands unlock millions in missed revenue - Work with top brands: Partner with category leaders like Brooklinen, Quay, and ColourPop - Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce Compensation & Benefits - Competitive base salary + commission package - Equity in a fast-growing, venture-backed company - Traditional medical/dental/vision/other healthcare coverage - 4 weeks PTO + health days - 401k plan - Monthly gym membership reimbursement - Company retreats and team get togethers - Remote-first culture (preference for those near major cities - NYC, LA, SLC, Miami, Chicago, etc.)

• Document and manage internal escalations, acting as the primary intake representative for incidents and drafting SOPs to prevent recurring disruptions • Monitor multiple queues simultaneously — from automation errors to same-day voids and cancellations — adjusting priorities in real time as conditions shift • Interpret travel advisories and coordinate workflows that process high volumes of schedule changes driven by disruptions or disasters • Communicate directly with airlines, hotel providers, HTS partners, and Hopper customers via phone, email, and chat to gather the information needed to resolve escalated concerns • Service complex bookings — including net fares, multi-ticket itineraries, and commission-based arrangements — often within the same PNR • Support Hopper-specific products like Cancel for Any Reason and Price Freeze, applying sound judgment to unconventional scenarios • Go beyond the playbook when needed — if a customer needs something you haven't handled before, you find a way

• Drive customer success by ensuring our clients enhance the safety, efficiency, and sustainability of their operations with our IoT platform. • Collaborate with customers to develop success plans, identify objectives, define metrics, and overcome barriers to business value realization. • Partners with cross-functional teams like Product, Support, Finance, etc. to drive progress on customer requests. • Facilitate executive business reviews to align on goals and celebrate successes with customers and Samsara leadership. • Conduct workshops to understand customer operations, recommend workflow enhancements, and maximize the value of Samsara products. • Develop a deep understanding of the Samsara platform's capabilities and effectively communicate them to diverse businesses across various industries. • Partner with cross-functional teams to address customer requests and drive progress on customer initiatives. • Serve as a mentor to the wider Customer Success team, championing Samsara's cultural principles.

• Develop, deploy, and manage complex, trigger-based customer journeys and automated workflows within HubSpot to deliver tailored, 1:1 customer experiences. • Treat AI as a core part of how the work gets done. Use AI to draft, personalize, segment, summarize, QA workflows, and surface insights more quickly than any team could manually. Pilot AI agents inside lifecycle touchpoints, evaluate new HubSpot AI features as they release, and bring back what proves valuable. The measure is not whether you used AI, but how much speed and quality it unlocked across your work. • Act as the steward for HubSpot data integrity. Implement automated data-cleaning processes, manage deduplication, oversee list hygiene, and manage the Salesforce/CRM integration sync and field mappings. • Maintain adherence to communication regulations (TCPA, CAN-SPAM) and champion email/SMS deliverability and sender reputation best practices. • Turn campaign performance into intelligence the business can act on. Build KPI reports that teams actually use. Surface meaningful trends early. Translate performance data into clear recommendations a leader can move on with confidence. The bar here is not reporting — it is intelligence that changes decisions.