Director of Sales

About ProShip
ProShip, Inc. is a market-leading provider of enterprise multi-carrier parcel shipping software, trusted by 30% of the National Retail Federation's Top 100 Shippers, including Kohl's, Ulta Beauty, QVC, Petco, and TJX. Founded in 2001 by two U.S. Navy veterans, ProShip built its platform on a simple belief: shipping is complicated, but it shouldn't have to be.

Today, ProShip's versionless, carrier-agnostic platform performs carrier rating, business-rule execution, and label printing in milliseconds — giving the highest-volume shippers in retail, e-commerce, manufacturing, healthcare, and third-party logistics the speed, intelligence, and reliability they need to turn shipping into a competitive advantage. As part of Vela Software Group (a division of Constellation Software), ProShip combines the agility and focus of an independent software company with the stability of a global technology portfolio.

Position Summary
ProShip is seeking a results-driven Director of Sales to lead new business growth for our enterprise shipping software platform. This is a high-impact, quota-carrying leadership role responsible for building and scaling a high-performing sales team, running complex enterprise sales cycles, and shaping go-to-market strategy across ProShip's core verticals — retail, e-commerce, 3PL/logistics, manufacturing, and healthcare. You will partner closely with executive leadership, marketing, product, and customer success to translate ProShip's technical differentiation into revenue growth.

Key Responsibilities

- Own and drive new business revenue targets for ProShip's enterprise shipping software solutions, managing full sales cycles from prospecting through close on complex, six- and seven-figure deals.

- Recruit, coach, and lead a team of sales and account executives; set individual and team quotas and hold the team accountable to activity, pipeline, and forecast accuracy metrics.

- Develop and execute territory- and vertical-specific go-to-market strategies across retail, e-commerce, 3PL, manufacturing, and healthcare shippers.

- Build and maintain a robust, accurately forecasted pipeline using disciplined CRM hygiene; deliver reliable weekly, monthly, and quarterly forecasts to executive leadership.

- Serve as a strategic, executive-level advisor to prospective enterprise customers — understanding complex shipping, fulfillment, and carrier-compliance challenges and positioning ProShip's platform (multi-carrier rate shopping, business-rule automation, LTL, hazmat, and label generation) as the solution.

- Partner with Marketing to refine messaging, campaigns, and lead-qualification criteria that reflect ProShip's positioning as “the last shipping software you'll ever need.”

- Collaborate with Product and Engineering, relaying market and customer feedback that helps shape the roadmap.

- Work closely with Implementation and Customer Success teams to ensure smooth handoffs, strong account health, and expansion opportunities within existing accounts.

- Represent ProShip at industry events, trade shows, and conferences to build brand awareness and generate pipeline.

- Negotiate enterprise contracts and pricing in partnership with Legal and Finance.

Qualifications

- 7+ years of B2B software/SaaS sales experience, including 3+ years in a sales leadership role carrying and exceeding a team quota.

- Proven track record selling complex, enterprise-level technology solutions with long sales cycles and multiple stakeholders (VP/C-suite, IT, and Operations).

- Experience in supply chain, logistics, parcel shipping, transportation management, e-commerce, or retail technology strongly preferred.

- Demonstrated success building and scaling a sales team, including pipeline management, forecasting discipline, and deal-qualification frameworks (e.g., MEDDIC/MEDDPICC).

- Strong executive presence with the ability to sell to and influence senior operations and IT decision-makers.

- Proficiency with CRM an