Senior Director, Sales Transformation

Role Overview

• Own and maintain AI strategy for Sales that is updated as the market moves, proactively adjusted for fast-moving market adjustments, backed by research and evidence.
• Be a pioneer
• seek out and review new solutions as a source of ideas and produce documented recommendations on what they mean for our strategy on an ongoing basis.
• Maintain always-ready strategy documentation with the vision for each sales persona, progress against it, and current market context, which can be presented to leadership anytime.
• Absorb context from senior leadership conversations and translate it into roadmap implications without needing to be walked through it.
• Own the business case for AI program spend, including a clear framework for how to allocate budget across platforms.
• Develop and maintain a KPI framework and cost-per-workflow model covering adoption, time savings, deal impact, and cost.
• Build a reporting cadence that keeps executives, IT leadership, and key stakeholders aligned on progress, risks, and decisions needed.
• Act as an internal product manager for AI in Sales by owning and driving the workflow mapping process across all sales roles.
• Connect 1:1, in focus groups, and via surveys with sales personas to understand pain points and opportunities for AI augmentation in workflows.
• Translate workflow maps and field input into feature requirements and work with IT to drive product development cycles.
• Design and run structured beta programs and close the feedback loop with participants while feeding findings back into the roadmap with transparency.
• Conduct ongoing workflow discovery with the field so that pain points are surfaced continuously.
• Serve as the primary point of contact from Sales with IT for all AI-related work while maintaining the relationship and communication flow.
• Oversee the team serving as the Sales organization's primary voice and stakeholder in the CRM migration project.
• Work with Sales Enablement to verify field-facing readiness for the go-live window and the hypercare period that follows.
• Maintain a clear view of what the L2C system enables for Sales over time, including how the new CRM foundation creates the data connectivity needed to accelerate the AI roadmap.
• Own a current view of every tool in the Sales technology ecosystem while rationalizing the tool stack against budget constraints.
• Partner with the Sales Enablement Team to ensure there is a phased change management plan for every tool or AI agent rollout.
• Communicate regularly across the org on strategy and progress to ensure the transformation is understood.
• Present independently to senior and C-level leadership in executive forums, owning the narrative and delivering an honest read on what is working and what is needed.

Requirements

• Bachelor's degree or higher
• 15+ years of relevant experience, with at least 10 years in leadership roles in SaaS environments
• Deep knowledge of how sales organizations operate: how they are structured, how sellers work day to day, and what field pain points look and feel like.
• Experience in sales operations or driving transformations for sales organizations, including knowledge of enterprise and commercial sales motions
• Demonstrated track record of driving multiple significant transformation initiatives to adoption — beyond launch — with clear lessons from where they stalled and what you would do differently.
• Experience being the person the field called when something broke, driving business validation and sign-off, and understanding what go-live and hypercare demand from a Sales stakeholder
• Hands-on experience deploying or overseeing AI solutions in a commercial context: gathering and translating requirements, pushing to production, and managing the adoption curve
• Product management or adjacent experience: writing requirements, managing a backlog, running structured feedback loops, and making tradeoff decisions under pressure
• Experience managing a Sales technology stack, including evaluating and rationalizing tools against budget constraints and a broader systems architecture, and building the business cases to support those decisions
• Hands-on experience with frontier AI platforms at a level beyond general awareness, with the ability to have a technical conversation about model capabilities, cost tradeoffs, and what frontier AI can and cannot reliably do in a sales workflow context
• Proficiency with Salesforce at a functional level, including how CRM workflows, personas, and access models are structured in an enterprise environment
• Strong leadership and interpersonal skills with excellent written, verbal, and presentation communication
• Demonstrated ability to build and develop high-performing teams across multiple workstreams through complexity and change, with a track record of facilitating the career growth of direct reports
• Demonstrated ability to operate independently and drive outcomes through influence, building relationships and gaining alignment across functions without relying on formal authority
• Experience working across complex organizations with stakeholders who have competing priorities
• A track record of presenting to senior and C-level leadership independently, owning the narrative, and incorporating feedback with composure
• Strong analytical mindset with experience leveraging data to drive decision-making and performance optimization
• Comfort operating at high pace with high visibility, being responsive outside of standard business hours, with occasional travel required
• Proficiency with standard productivity and project management tools (Microsoft Office suite, project planning software, or equivalent)
• Experience working with cloud technologies, digital transformation initiatives, and agile delivery methodologies
• Comfort learning rapidly in an environment where the technology, market, and organizational priorities are all evolving simultaneously.

Tech Stack

• Cloud

Benefits

• Medical, Dental, and Vision Insurance.
• Telehealth coverage
• Flexible work schedules and work from home opportunities
• Development and career growth opportunities
• Open Time Off in addition to 10 paid holidays
• 401(k) matching program
• Adoption Assistance
• Fertility treatments