Senior Director, Sales AI Strategy – Transformation

This is a fully remote position, open to applicants in California, +3 more states.

📋 Description

• Spearhead the AI transformation of Sales workflows and strategies by engaging in the hands-on design and development of autonomous solutions.

• Take ownership of the Sales AI strategy, encompassing the long-term vision, business case, KPI framework, cost-per-workflow model, and investment roadmap.

• Create prototypes for workflows, assess model behaviors, collaborate with engineers to define requirements, and facilitate the transition of solutions to production.

• Manage workflow mapping across various sales roles while maintaining a prioritized backlog and roadmap.

• Conduct workflow discovery sessions through one-on-one interviews, focus groups, and surveys with sales personas.

• Convert workflow maps and field insights into feature requirements, driving product development cycles in partnership with IT.

• Design and execute beta programs, collect participant feedback, and incorporate findings into the product roadmap.

• Establish and operate a cross-functional model that integrates Sales, IT, and Enablement.

• Define sprint cadences, backlog grooming processes, stakeholder reviews, escalation paths, RACI frameworks, and reporting schedules.

• Act as the primary contact for AI-related initiatives within the Sales department.

• Collaborate with Sales Enablement on change management, role-specific training, certification, adoption support, and feedback mechanisms.

• Communicate the strategy and progress within the organization, independently presenting recommendations to senior and C-level executives.

• Lead and develop teams across multiple workstreams amidst transformation and organizational complexities.

• Monitor adoption rates, workflow time efficiencies, deal impacts, costs, and ROI associated with each use case.

⛳️ Requirements

• A Bachelor's degree or higher is required.

• Over 15 years of relevant experience, with a minimum of 10 years in leadership roles within SaaS environments.

• Practical experience in building or deploying autonomous AI solutions in a commercial setting.

• Hands-on familiarity with cutting-edge AI platforms, coupled with the ability to discuss model capabilities, cost trade-offs, and reliability within sales workflows.

• Experience in product management or related roles, specifically managing backlogs and roadmaps, drafting requirements, managing trade-offs, and conducting feedback loops.

• Proven experience in designing and implementing operating models that minimize friction and expedite delivery.

• In-depth understanding of sales organizational structures, seller workflows, and field challenges.

• Background in sales operations or sales organization transformation, including enterprise and commercial sales processes.

• A strong record of driving substantial transformation initiatives through effective adoption strategies.

• Experience with business validation, sign-off processes, go-live phases, and hypercare from the perspective of Sales stakeholders.

• Competence in managing a Sales technology stack and creating tool evaluation and investment business cases.

• Functional knowledge of Salesforce, including enterprise CRM workflows, personas, and access models.

• Excellent written, verbal, presentation, leadership, analytical, and interpersonal skills.

• Proven ability to build and cultivate high-performing teams across multiple workstreams.

• Capability to work independently, influence cross-functional teams, and achieve alignment without formal authority.

• Experience navigating complex organizations with competing priorities.

• History of presenting independently to senior and C-level executives.

• Comfort in operating at a fast pace and high visibility, including responsiveness outside of normal business hours.

• Occasional travel may be necessary.

• Proficiency in Microsoft Office, project planning software, or comparable productivity and project management tools.

• Experience with cloud technologies, digital transformation initiatives, and agile delivery methodologies.

• Ability to quickly learn in response to evolving technology, market conditions, and organizational priorities.

🏝️ Benefits

• Medical, Dental, and Vision Insurance.

• Telehealth coverage.

• Flexible work schedules and options to work from home.

• Opportunities for development and career growth.

• Open Time Off policy in addition to 10 paid holidays.

• 401(k) matching program.

• Adoption Assistance.

• Fertility treatment support.

• Access to mentorship, learning programs, leadership development, and educational support.

• Paid volunteer time.

• August Free Fridays.

• Well-being resources available.

• Regionally tailored programs for employees and their families.

• Potential eligibility for commission or performance-based bonus opportunities.