VP/Sr. DIRECTOR, Enterprise Sales (Player Coach)

VP/Sr. DIRECTOR, Enterprise Sales (Player Coach) JOB TITLE: Director or Vice President of Sales LOCATION : San Diego, CA; On-Site ; Full Time TO BE CONSIDERED: Send a Cover Letter and Resume to Write the Job Role in the Subject of your email. One-click LinkedIn Applications will NOT be considered. TOOTRiS is the nation's largest, tech-enabled child care benefits provider. We empower enterprise organizations across diverse industries—including manufacturing, healthcare, technology, government, and finance—to offer turn-key childcare solutions to their employees. TOOTRiS streamlines the management of these benefits through our innovative technology, assisting parents in using their employer-sponsored benefits with child care providers nationwide. We are in search of a dynamic leader to take our enterprise sales to the next level using past experience and industry knowledge to build and lead a team of Sales Executives and Account Managers. This person will bring with them the lessons learned from past wins and losses and the hunger to exceed expectations leading by example… If that’s you, we invite you to apply and be an integral part of our dedicated team committed to excellence. Position Overview: This is a critical leadership role focused on building and managing a high-performing enterprise sales organization. The Director will be responsible for developing and executing sales strategies, managing key client relationships, and acting as a strategic liaison between enterprise clients and internal TOOTRiS teams. This role will also encompass a player-coach dynamic , requiring the Director to both lead the team and actively engage in direct sales activities, including managing key accounts and driving significant deals to closure. The ideal candidate will have a demonstrated track record of building and leading successful enterprise sales teams, consistently exceeding sales targets, and penetrating complex enterprise accounts. This role requires a strong understanding of enterprise sales cycles, exceptional negotiation skills, and the ability to build and foster long-term, strategic partnerships with key decision-makers within large organizations. The Senior Sales Director will be instrumental in driving TOOTRiS's growth within the enterprise market, both through strategic leadership and direct sales contributions. RESPONSIBILITIES: ·      Lead and build a high-performing sales team from the ground up, nationally, expanding to a substantial workforce. Utilize your extensive SAAS sales experience and relationships to enhance the national footprint. ·      Implement and refine end-to-end sales processes, utilizing a hands-on and scientific approach to building a robust pipeline. Execute strategic account plans to drive success and foster long-term partnerships. ·      Act as a dedicated advocate for clients within our organization, ensuring seamless communication, effective resolution of issues, and a consultative approach to understanding clients' evolving needs. ·      Provide formal training on sales processes, leveraging your expertise to mentor and guide the team. Utilize your relationships and experience with SAAS sales across industries. ·      Develop and implement strategic plans to maximize the impact of our Child Care solutions, aligning seamlessly with clients' goals and contributing to the well-being of working families. REQUIRED EXPERIENCE: Sales Experience: o  Minimum of 3 to 5 years of hands-on experience in SAAS or benefits sales. o  Proven track record of achieving and exceeding sales targets. Leadership Experience: o  Success in building a team of experienced professionals , fostering a collaborative and high-performing sales environment o  Previous experience leading a team of at least 5 with a national footprint ·      A leadership style that values autonomy, enabling team members to excel independently. ·      A hands-on and scientific approach to crafting and executing sales pipelines, ensuring a methodical and data-driven strategy. ·      Proven ability and willingness to personally engage in sales activities, stepping in when needed close deals to achieve organizational objectives. PREFERRED EXPERIENCE: ·      Previous familiarity with the Benefits and/or Insurance industry. ·      Understanding of the unique challenges and opportunities in the child care sales landscape. ·      In-depth knowledge of the Child Care business landscape and regulatory environment. ·      Prior experience as a client advocate, ensuring effective communication and issue resolution. o  Familiarity with innovative solutions that align with business objectives in the context of Child Care services. ·      Familiarity with Salesforce or similar CRM tools. ·      Formal training in advanced sales processes, including recognized programs such as Miller Heiman Training, demonstrating a commitment to excellence. COMPENSATION: $275,000 OTE uncapped BENEFITS: ·      Child Care Benefit ·      Medical, Vision, & Dental Insurance ·      Unlimited PTO *after 120-day cycle* ·      11 Holidays + Birthday off ·      401K plan ·      Equity/Options Important Details TOOTRiS is Committed to creating an environment where employees thrive. It's why we provide every employee with unlimited PTO as of your 120 th day of employments, private health insurance, and a 401K plan and of course, Child Care as a Benefit

Created: 2025-10-02