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 and sales engagement tools (e.g., Salesforce, HubSpot, Outreach).
• Excellent negotiation, communication, and cross-functional collaboration skills.
• Willingness to travel approximately 25–30% for client meetings, industry events, and trade shows.

Preferred Qualifications

• Existing network of relationships among retail, e-commerce, 3PL, or manufacturing logistics and IT decision-makers.
• Bachelor's degree in business, supply chain, or a related field, or equivalent professional experience.
• Familiarity with parcel carriers (UPS, FedEx, USPS, and regional carriers) and shipping compliance requirements.
• Experience selling into organizations shipping 1,000+ parcels per day.
• Formal sales methodology certification (e.g., MEDDIC, MEDDPICC, Challenger).

What ProShip Offers

• Competitive base salary plus uncapped commission/OTE
• Comprehensive health, dental, and vision coverage
• 401(k) with company match
• Generous paid time off and holidays
• The opportunity to lead growth at an established, market-leading company backed by a global software portfolio (Vela Software Group / Constellation Software)
• A collaborative, tenured team with deep expertise in shipping and logistics technology

ProShip, Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.