Enterprise Sales Executive
Listed on 2026-02-18
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Business
Business Development
About Openforce
Openforce®is the leading compliance and workforce management software and payments processing platform for managing the commercial relationships between contracting companies and independent contractors (ICs). Its cloud-based software is a vital tool that empowers contracting companies to operate with confidence by addressing compliance risks and lowering operational costs through AI-powered onboarding, insurance enablement, contracting, and settlement processing (including vendor invoicing and deduction management) technology.
In addition, Openforce provides customized insurance solutions tailored to ICs and critical business tools that ICs need to manage their small businesses and increase their profits. By joining Openforce, you'll play a key role in helping enterprise-level contracting companies leverage Openforce’s turnkey solution set.
About Openforce
Openforce®is the leading compliance and workforce management software and payments processing platform for managing the commercial relationships between contracting companies and independent contractors (ICs). Its cloud-based software is a vital tool that empowers contracting companies to operate with confidence by addressing compliance risks and lowering operational costs through AI-powered onboarding, insurance enablement, contracting, and settlement processing (including vendor invoicing and deduction management) technology.
In addition, Openforce provides customized insurance solutions tailored to ICs and critical business tools that ICs need to manage their small businesses and increase their profits. By joining Openforce, you'll play a key role in helping enterprise-level contracting companies leverage Openforce’s turnkey solution set.
Position Summary
As an Enterprise Sales Executive, you will be responsible for driving net-new revenue by engaging large, complex organizations that rely on independent contractors to deliver their services. You will lead consultative sales motions that educate prospects on compliance risk, operational inefficiencies, and the financial implications of managing a 1099 workforce—positioning Openforce as the system of record for contractor onboarding, compliance, insurance enablement, and settlement processing.
This role is ideal for a seasoned SaaS seller who excels in multi-stakeholder enterprise sales, is comfortable navigating regulated or compliance-heavy environments, and can translate complex product capabilities into clear business outcomes.
Responsibilities
- Own and drive the full enterprise sales lifecycle, from targeted prospecting and discovery through deal close and handoff to implementation teams
- Build trusted relationships with executive-level stakeholders, positioning Openforce as a strategic partner for independent contractor workforce management and risk mitigation
- Lead structured discovery to uncover operational, compliance, financial, and scalability challenges tied to 1099 workforce models
- Deliver tailored product demonstrations and solution narratives aligned to each prospect’s business model and contractor engagement strategy
- Develop and present compelling business cases that clearly articulate ROI, risk reduction, and operational efficiency gains
- Maintain disciplined pipeline management, accurate forecasting, and consistent attainment of quarterly and annual revenue targets
- Stay current on independent contractor compliance trends, regulatory developments, and market dynamics to effectively advise enterprise buyers
- Collaborate cross-functionally with marketing, product, legal, and implementation teams to support complex deal requirements and successful customer outcomes
Requirements
- 4+ years of experience selling enterprise SaaS solutions with complex, multi-stakeholder buying cycles
- Proven ability to manage long sales cycles, navigate ambiguity, and drive deals forward with structure and urgency
- Strong consultative selling, discovery, and executive communication skills
- Track record of meeting or exceeding revenue targets in a growth-oriented, high-accountability environment
- Demonstrated success selling into organizations that utilize large 1099 or contractor-based work forces strongly preferred
- Experience selling into regulated or compliance-sensitive environments (e.g., logistics, field services, healthcare, marketplaces) strongly preferred
We offer a competitive compensation package, flexible work options, and the opportunity to make a meaningful impact on the evolving landscape of independent contractor workforce management. At Openforce, you’ll be part of a team dedicated to helping companies adapt to modern workforce needs with innovative compliance and workforce management-driven solutions.#J-18808-Ljbffr
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