---
title: 'Director, Software Sales- Upper Mid-Market at Versapay'
canonical: 'https://feeny.ai/job/director-software-sales-upper-mid-market-versapay-canada-px5nj5hvgfhv'
type: 'job'
last_seen: '2026-09-10'
---

# Director, Software Sales- Upper Mid-Market at Versapay

- **Company:** Versapay
- **Location:** Canada
- **Compensation:** $160k–$180k
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-07-20
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.lever.co/versapay/35b29712-6361-4dae-8e0f-67587b906d0c

## Job description

## About Versapay 🚀

Versapay turns accounts receivable (AR) into a competitive advantage.

Inefficient AR processes slow cash flow and stall growth. Versapay removes friction, unlocks working capital, and accelerates momentum — giving finance leaders the clarity and control they need to drive business forward.

Versapay automates accounts receivable, removing barriers to collecting and reconciling B2B payments. Our solutions connect finance teams, customers, and business systems in one ecosystem to ensure cash flow clarity. With over 10,000 customers and 5M+ companies transacting on the platform, Versapay processes over 110M transactions and $257B annually.

Think you might be the next Veep to join? Read on!!

## About the Role

As the Director of Software Sales - Upper Mid-Market, you will lead Versapay’s strategy to grow new bookings and revenue across $100M+ companies. You will build and scale a high-performing team of Software AEs, drive execution across Sales Development and strategic partner channels, and own the Upper Mid-Market team’s annual revenue target. Partnering closely with Sales, Marketing, Product, Finance, and Partner teams, you will translate market opportunity into repeatable sales motions, stronger partner leverage, and measurable revenue outcomes. This role requires deep fintech expertise, strong software sales leadership, and the ability to build strategic relationships that create value for customers, partners, and Versapay.

What you'll do:

- Coach and executive sponsor a team of highly skilled and passionate Software Sales AEs responsible for closing multi-threaded deals referred by SDRs, FVARs, and Strategic Partner Sales Teams to maximize sales.
- Deploy best-in-class sales strategies and processes and co-create and execute the blueprint for the team’s success.
- Act as the primary point of contact for Software prospects’ inquiries, concerns, and escalations.
- Negotiate high-value software agreements and terms to ensure favorable outcomes for both customers and Versapay.
- Maintain a deep understanding of the pains we solve and how to build a business case for change with prospects.
- Collaborate with Marketing and Partner teams to leverage partner relationships, meet bookings targets, and develop joint marketing initiatives, co-selling opportunities, and co-development projects.
- Establish key performance indicators (KPIs) and operating mechanisms to continuously measure sales success and partnership effectiveness.
- Monitor sales team performance and track progress toward achieving targets.
- Provide regular reports and updates to senior management on sales activities and outcomes, including conversion rates, pipeline generated, and pipeline closed.
- Collaborate cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Sales Support, Underwriting, and Implementation teams.
- Collaborate with the Product Development team to ensure product-market fit and confirm that integrations are working effectively for mutual clients.

What you'll bring to the team:

Required

- 7+ years of experience working for a fast-paced SaaS or Fintech company.
- 5+years of experience leading a SaaS Sales team.
- 3+ years of experience leading an Upper Mid Market or Enterprise team.
- 5+ years of experience negotiating directly with Finance leaders as part of the core buying persona, including Controllers, VPs of Finance, CFOs, CTOs, CIOs, and/or CAOs.
- Experience implementing, reinforcing, and providing ongoing coaching using a proven sales methodology, with deep knowledge of the sales process from discovery through solutioning, ROI discussions, executive proposals, negotiation, closing, and implementation team handoffs.
- Proven track record building relationships with key decision makers, moving opportunities forward, delivering results, and exceeding quota.
- Experience working with and leading virtual teams across functions and geographies.
- Experience creating operational rigour and identifying and replicating core KPIs.
- Experience in the payments industry is a plus.

## Preferred

- Passion for sales and all things sales-related.
- Excellent at building strong relationships and collaborating with others.
- Ability to prioritize multiple projects, opportunities, and personalities across the deal cycle.
- Problem-solving mentality: you leverage internal and/or external resources, resolve conflicts, and follow through with partners.
- Naturally curious and confident, you ask thoughtful questions, listen, learn from conversations, and use those insights to evangelize how innovative fintech solutions can help partners and prospects on their path to digital transformation.
- Very comfortable with Salesforce reporting and working with both structured and raw data to understand the business well enough to grow and exceed targets.
- Well organized, you manage many moving pieces at once, often coordinating internal teams to bring the best Versapay can offer to clients.
- Bias toward action: you love to dive in and get things done.
- Comfortable working with people at any level in the organization, you nurture relationships as needed and become a trusted advisor.
- Competitive attitude with experience crushing a sales quota; you love closing deals.

#LI-Remote

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

## About Versapay

## Company Overview
- **One-liner**: Versapay provides a fully unified accounts receivable automation platform that simplifies the invoice-to-cash process for B2B businesses.
- **Entity Type**: Private (funding stage not disclosed in provided sources)
- **Headquarters**: Remote-first; team distributed across Canada, the United States, and Israel (no physical offices; HQ not explicitly listed)
- **Founded**: Not publicly available from provided sources
- **Founders**: Not publicly available from provided sources

## Core Business
- **Primary industry**: Accounts receivable automation, B2B payments, financial technology
- **Target customers**: B2B finance teams, accounts receivable departments, enterprises, and SMBs
- **Mission or purpose**: “To remove financial friction so that business ecosystems transact smarter, faster, and with greater resiliency.”

## Products & Services
- **Accounts Receivable Automation Platform**: A unified SaaS platform covering invoicing, collections, cash application, B2B payments, and reporting/reconciliation. Includes AI-powered automation, a self-service customer portal, and deep ERP integration.
- **B2B Payment Services**: Accept ACH, credit cards, and wire payments with flexible payment rules, fraud monitoring, and early payment discounts.
- **Collections Management**: Automated dunning, delinquency prediction, and prioritization of high-risk accounts.
- **Cash Application & Reconciliation**: Automatic matching of payments to invoices regardless of remittance method, with straight-through posting to ERP.

## Market Standing
- **Valuation/Market Cap**: Not publicly available
- **Key Metric**: Processes over **$170B** in payments volume annually; serves **10,000+** customers and facilitates transactions for **5M+** companies; handles **110M+** transactions per year.
- **Notable Investors/Partners**: Mastercard, US Bank, and other payment processors and ERP vendors (specific investors not detailed in provided sources).
- **Growth Signals**: Fully remote, global hiring (e.g., Customer Success Manager, Principal .NET Software Engineer); expanding platform capabilities with AI; strong partner ecosystem.

## Competitive Advantages
- **Unified end-to-end platform** covering the entire invoice-to-cash cycle, reducing the need for multiple vendors.
- **AI-driven automation** for collections, cash application, and forecasting.
- **Deep ERP integration** enabling straight-through processing and real-time posting.
- **Large B2B payment network** (5M+ companies transacting) creating network effects.
- **Remote-first culture** with no return-to-office mandates, attracting top global talent.

## Strategic Focus
- Continue to remove friction in accounts receivable through AI, automation, and integrated payments.
- Expand partnerships with major payment networks and ERP providers.
- Scale the platform to serve larger enterprises while maintaining ease of use for SMBs.
- Drive cash flow confidence and financial resiliency for customers.

## Why Work Here
- **Remote-first environment** with no office mandates; employees work from anywhere in Canada, the US, or Israel.
- **Flexible PTO and sick time** to support work-life balance.
- **Competitive compensation** with annual performance bonuses for all employees.
- **Benefits**: RRSP (Canada) and 401k (US) contributions, robust health benefits.
- **Culture**: Virtual and in-person events (town halls, team meetups, offsites, retreats); tools like Slack, Teams, and Bonusly for collaboration and peer recognition.
- **Growth opportunities**: Roles across engineering, product, customer success, and more; emphasis on divergent thinking and async workflows.

## Sources
1. [Versapay Careers Page](https://www.versapay.com/careers)
2. [Versapay Product Page](https://www.versapay.com/)
3. [Versapay Job Listings (Lever)](https://jobs.lever.co/versapay)
4. [Versapay About Us](https://www.versapay.com/about-us)
5. [Versapay Leadership](https://www.versapay.com/leadership)

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