Director of Sales

Paystand•Miami, FL

5h•Onsite

About The Position

At Paystand, we’re not just another fintech company—we’re trailblazers in decentralized finance (DeFi), transforming how businesses manage their finances. With thriving hubs in Santa Cruz, San Francisco, Austin, Minneapolis, Mexico City, Hermosillo, and Guadalajara, we’re leading a global revolution in financial systems. Recognized on the Inc. 5000 list for five consecutive years, we’re among the fastest-growing companies reshaping the future of finance. Our Expanding Ecosystem: Paystand isn’t just a company—it’s a growing global network. With the strategic acquisitions of Teampay, a leader in spend management, and Yaydoo, a top AR and AP platform in Latin America, we’re building an expansive ecosystem designed to revolutionize financial operations and fuel business growth worldwide. Why Paystand? What We Do: By harnessing the power of blockchain technology, we digitize receivables, automate financial processes, reduce time-to-cash, lower transaction costs, and unlock new revenue streams for businesses. Why We Do It: We’re driven by a mission to revolutionize digital payments and decentralize finance, creating a more open, inclusive, and transparent financial ecosystem, starting with B2B payments. How We Do It: As change-makers in the DeFi movement, we don’t just follow trends—we set them. If you’re passionate about shaping the future of fintech and eager to redefine what financial technology should look like, Paystand is the place where you can make a significant impact. Join Us: Be part of something bigger. Join Paystand and help us lead the financial revolution. Role at a Glance As Director of Sales, you will lead revenue execution for Bitwage, a high-growth, early-stage business unit within Paystand. You will own the sales motion end-to-end—managing and scaling a team of inbound and outbound sales representatives, driving partner-led revenue, and personally closing complex, high-value deals. This role combines the ownership and intensity of an early-stage startup with access to late-stage resources, capital, and cross-functional expertise. You will work closely with the Founder & GM of Bitwage and senior leaders across Paystand to define go-to-market strategy, build a repeatable sales engine, and deliver against aggressive, board-visible revenue targets. You will play a critical role in transitioning Bitwage from founder-led sales to a scalable, metrics-driven revenue organization—while remaining hands-on in the field and deeply involved in hiring, coaching, and performance management. About Bitwage & Paystand Bitwage is a global payroll and cross-border payments platform that enables companies to pay employees and contractors in local currencies, stablecoins, and cryptocurrency—faster, cheaper, and with significantly less friction than traditional banking rails. Bitwage serves globally distributed teams across 80+ countries and operates at the intersection of fintech, payments, and crypto infrastructure. Bitwage operates as a high-growth, early-stage business unit within Paystand, a later-stage B2B payments company backed by leading investors. This structure provides a unique environment that combines: ● Startup speed, ownership, and impact within Bitwage ● Operational maturity, capital, and shared resources from Paystand This role is ideal for a sales leader who wants to build and scale from an early foundation while benefiting from the stability, tooling, and institutional knowledge of a more established organization. Why This Role Is Unique ● Build a sales organization from the ground up at Bitwage, with real ownership over strategy, hiring, and execution ● Operate in an early-stage environment while benefiting from Paystand’s: ○ Established infrastructure and systems ○ Legal, compliance, finance, and operational support ○ Institutional knowledge from scaling a B2B payments business ● Gain direct visibility with executive leadership and influence over product, pricing, and roadmap ● Career-accelerating opportunity to prove you can scale revenue in a complex fintech environment Why This Role Matters This is a career-defining opportunity to build and lead a revenue engine at an early-stage fintech solving real problems in global payments. You will have meaningful ownership over strategy, hiring, execution, and outcomes—along with a direct line to the GM of Bitwage and Senior Leadership. If you're passionate about driving change in the FinTech landscape and being part of a company that is shaping the future of digital payments, we invite you to explore opportunities with Paystand. We understand that no candidate is perfectly qualified for any job. Experience manifests in diverse ways, skills are transferable, and passion is a powerful driver. Your journey and skills are unique, and we value the richness that diverse perspectives bring to our team. More than a resume, we prioritize a genuine commitment, impactful contributions, and the ability to thrive in our dynamic, collaborative environment. We are enthusiastic about providing you with opportunities to learn and grow within this role. If your experience aligns closely with what we're seeking, we encourage you to apply. We celebrate the belief that diversity in backgrounds and thoughts fuels better problem-solving and fosters more creative thinking. Our commitment to adding new perspectives to the team reflects our dedication to innovation and inclusivity. Your journey is important to us, and we look forward to the possibility of welcoming you to our team at Paystand. Feel free to reach out; we can't wait to hear from you.

Requirements

7+ years of B2B sales experience, with at least 3+ years in a sales leadership or management role
Proven experience selling cross-border payments, fintech, payroll, FX, or financial infrastructure products
Experience working at a Series A startup or earlier, ideally during the transition from founder-led sales to a repeatable sales motion
Demonstrated success building, managing, and scaling sales teams in high-growth environments
Track record of closing complex, multi-stakeholder deals involving legal, finance, compliance, and operations
Strong understanding of long sales cycles, procurement processes, and fintech buying friction
Hands-on experience with CRM systems and sales performance metrics
Builder mentality; comfortable creating structure where none exists
Hands-on leader who leads by example and closes deals
High tolerance for ambiguity and rapidly changing priorities
Data-driven but pragmatic; able to forecast without perfect systems
Direct, candid communicator who embraces accountability
Motivated by ownership, equity upside, and long-term impact—not just title or base salary

Nice To Haves

Experience selling into globally distributed teams, emerging markets, orinternational workforces
Familiarity with compliance concepts such as KYC, AML, OFAC, and regulatory risk in payments
Prior experience owning or contributing to partnership-led revenue
Experience closing mid-market to enterprise deals ($50k–$250k+ ARR)

Responsibilities

Own overall sales performance, pipeline health, forecasting accuracy, and revenue outcomes
Lead and manage a team of inbound and outbound sales representatives, with planned growth from ~3 to ~8 team members within 12 months
Carry a personal quota and remain actively involved in closing strategic, complex, or high-value deals
Conduct regular pipeline reviews, forecast calls, and performance coaching sessions
Establish clear KPIs, quotas, and performance standards for the sales team
Build and continuously refine sales playbooks, including: ○ ICP definition and segmentation ○ Buyer personas and use cases ○ Discovery frameworks and qualification criteria ○ Pricing, packaging, and objection handling
Implement and enforce strong CRM discipline
Design scalable inbound and outbound sales motions suitable for an early-stage product within a late-stage corporate environment
Improve conversion rates across the full funnel, from first meeting through close
Own hiring, onboarding, ramping, and performance management of sales team members
Make hiring and termination decisions quickly and decisively to maintain a high-performing team
Develop 30-60-90 day ramp plans and ongoing training programs for new hires
Build a sales culture focused on accountability, ownership, and continuous improvement
Identify, evaluate, and develop revenue-generating partnerships (e.g., fintech platforms, payroll providers, SaaS platforms, ecosystem partners)
Structure partnership agreements with clear commercial incentives and pipeline expectations
Manage partner relationships and hold partners accountable to measurable revenue outcomes
Sunset partnerships that do not generate meaningful pipeline or closed-won revenue
Partner closely with Product, Engineering, Compliance, and Operations teams to: ○ Address customer feedback and objections ○ Improve onboarding and implementation workflows ○ Align product roadmap with market demand
Provide structured feedback from prospects and customers to inform product and pricing decisions
Collaborate with Marketing on messaging, positioning, and lead quality improvements
Own revenue forecasting and pipeline reporting with a high degree of accuracy
Prepare revenue updates for executive leadership and board meetings
Identify risks and opportunities early and adjust strategy proactively