The Strategic Sales Representative is responsible for developing and executing a targeted enterprise sales strategy focused on large organizations with $500M+ in revenue. This role drives revenue growth by identifying, pursuing, and closing complex opportunities across multiple business units or entities within the same corporate structure.

The Strategic Sales Representative will lead long-cycle, consultative sales efforts, manages executive relationships, and coordinate internal resources to deliver customized SaaS solutions aligned to each client’s strategic objectives. They own the end-to-end sales process, maintain accurate forecasting, and ensure enterprise clients experience a cohesive, value-driven journey that supports both initial land and ongoing expansion opportunities across divisions.

Key Responsibilities:

Develop and execute account-based strategies for targeting and penetrating organizations with $500M+ in revenue, including multi-entity and multi-division structures.

Identify, qualify, and manage complex, high-value SaaS opportunities across multiple business units within large enterprises.

Lead full-cycle, consultative enterprise sales processes from prospecting and discovery through solution design, proposal, negotiation, and close.

Navigate multi-stakeholder buying committees, including executive, technical, procurement, and finance stakeholders, to align on business case and decision criteria.

Build and maintain trusted advisor relationships with senior leaders (e.g., CIO, CHRO, COO, CFO) to support long-term strategic partnerships.

Partner with solutions engineering, product, customer success, and legal teams to design and deliver tailored proposals, pricing, and contracts that meet client requirements.

Maintain a disciplined, transparent pipeline; update CRM consistently; and deliver accurate forecasts and territory plans.

Achieve and exceed assigned quota, focusing on both new enterprise logo acquisition and expansion within existing accounts.

Stay current on product capabilities, integration options, competitive landscape, and market trends to effectively position the platform in enterprise environments.

Skills and Experience Needed:

Bachelor’s degree in business, technology, or a related field; advanced business education is a plus.

10-15+ years of full-cycle B2B SaaS sales experience, including 8+ years selling into enterprise organizations with $500M+ in revenue.

Demonstrated success closing large, complex, multi-stakeholder deals, ideally six- or seven-figure ACV.

Experience selling into multi-organization or multi-business-unit environments with complex governance and procurement.

Strong command of value-based, consultative selling methodologies (e.g., MEDDIC, Challenger, SPIN) and enterprise sales best practices.

Excellent communication, negotiation, and executive presentation skills, with the ability to influence C-level stakeholders.

High degree of technical acumen and ability to collaborate effectively with product and technical teams on solution design.

Competencies:

Accountability

Adaptability

Applied Learning

Business Acumen

Collaboration

Customer Focus

Dealing w/Ambiguity

Decision Making

Driving for Results

Initiating Action

Planning and Organizing

Technical/Professional Knowledge

About the company:

Boards set the standard for what organizations can achieve. At OnBoard, our board management software helps boards function at a higher level so every organization can make a bigger difference in the world.

Launched in 2011, today, OnBoard serves as the board intelligence platform for more than 5,000 organizations and their 12,000 boards and committees in 60 countries worldwide. With customers in higher education, nonprofit, healthcare systems, government, and enterprise business, OnBoard is the leading board management provider.

OnBoard has grown from a class project at Purdue University in West Lafayette, Indiana in 2003 into the world’s leading board management software platform today. Backed by JMI Equity and the acquisitions of eScribe and Govenda, OnBoard is positioned to become the industry leader in Board Management and Meeting Solutions for private and public sector entities.

Benefits and Perks:

Company provided equipment (laptop, software, etc.)
Employment with a growing, casual, fun, philanthropic minded company
Employer paid extended health benefits, including health spending account (CAN based employees)
US Based Employees
- Comprehensive, high-quality medical/prescription drug plan options, as well as dental and vision plan offerings.
- An employer contribution to your Health Savings Account (HSA) if you participate in a High Deductible Healthcare Plan.
- Medical Flexible Spending Accounts available.
- Dependent Care Flexible Spending Accounts available.
- Basic life insurance in the amount of $50,000 or 1 X’s your salary (whichever is higher).
- Short and long-term disability and Accidental Death and Dismemberment benefits at no cost to you.
- 401K Retirement Savings Plan with automatic enrollment at the first of the month following 60 days of employment at 5% to help you secure your financial freedom. We offer a generous company match that starts on the first of the month following 60 days of employment. The company match is dollar for dollar on the first 3% of your pay that you contribute and $0.50 on the dollar on the next 2%, for a total match of 4%.
- Paid Time Off (PTO)/Holiday

Diversity Statement - Culture of Togetherness:

At OnBoard, our mission is to encourage and celebrate a culture of togetherness. We acknowledge that uniqueness is powerful, and we welcome, foster, and appreciate all. Diversity, Equity, and Inclusiveness fuel the Pathfinder atmosphere and all our efforts. Our power is in our people and we Pledge 1% to give back to our communities and across the globe.

OnBoard is an equal opportunity employer and committed to a diverse and inclusive working environment. Passageways does not discriminate based on race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. For individuals with disabilities who would like to request an accommodation please email peopleops@passageways.com.

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