Director of Sales

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

Responsibilities
Sales Leadership & Execution
● 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

Sales Process & Playbook Development
● 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

Hiring, Team Development & Performance Management
● 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

Partnerships & Channel Revenue
● 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

Cross-Functional Collaboration
● 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

Forecasting, Reporting & Executive Communication

● 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

Qualifications & Experience
Required
● 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

Preferred / Nice to Have
● 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)

Traits & Mindset We’re Looking For
● 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

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.