Head of AI Value Strategy

Summary

Join Outreach as the Head of AI Value Strategy, reporting to the Chief Revenue Officer. You will engage with C-suite leaders to understand their needs and offer Outreach's AI-powered solutions. This customer-facing role involves scaling product positioning and sales, educating the sales team on selling AI products, and focusing on value outcomes. The ideal candidate possesses a background in AI development/engineering, sales engineering, sales management, value consulting, or revenue strategy. You will be responsible for leading strategic value engagements, go-to-market planning, sales enablement, competitive differentiation, and performance tracking. The role requires strong executive presence, expertise in building business cases, and a deep understanding of enterprise SaaS business models and AI trends. Location is open to remote within the US.

Requirements

• 8+ years in sales engineering, value consulting, management consulting, solution consulting, or strategic sales roles—ideally at a B2B SaaS or AI-focused company
• Expertise in building business cases, financial models, and C-level narratives that translate technology into business value
• Strong executive presence and experience engaging VP+ and C-suite stakeholders. Ideally has a rolodex of C-Suite contacts and leaders that they have already built trust with
• Deep understanding of enterprise & global SaaS business models, AI trends, and go-to-market dynamics
• Know how to differentiate ina fast-moving, crowded AI space
• Familiarity with AI/ML concepts and comfort working with technical stakeholders
• Exceptional storytelling, communication, and facilitation skills
• Analytical mindset with the ability to synthesize data into insights and strategic recommendations
• Experience working in high-growth, fast-paced startup environments
• Strong understanding of enterprise sales motions and tools used by revenue teams
• Experience selling against competitive and build-vs-buy scenarios

Responsibilities

• Lead strategic value engagements with prospective and current enterprise customers, focusing on aligning our AI solutions with their top business priorities and challenges. You’ll guide discussions that uncover economic, operational, and competitive drivers
• Help lead end-to-end go-to-market planning for Outreach AI features and solutions
• Aid in defining packaging, value messaging, and sales plays aligned to priority segments and verticals
• In Partnership with the Enablement team, create sales enablement content and training to ensure AI capabilities are positioned as deal accelerators
• Partner closely with sales and enablement to coach managers, SEs, and AEs on how to articulate the value of AI in discovery, demos, and proof-of-value engagements
• Assist in creating battlecards and objection-handling tools that help teams confidently navigate AI-focused evaluation cycles
• Develop positioning frameworks to clearly differentiate Outreach AI from: New AI-native platforms entering the sales tech space, Internal AI solutions being built by customers' RevOps or IT teams using LLMs, BI platforms, or open-source tools
• Build competitive plays and partner with product marketing to arm the field with intel, win stories, and proof points
• Establish thought leadership by contributing to whitepapers, customer success stories, and event presentations that illustrate the transformative business value of our AI platform
• Track AI-influenced pipeline and revenue in partnership with RevOps
• Build customer value realization stories that connect Outreach AI with concrete business outcomes (e.g., improved seller productivity, faster ramp, better conversion)
• Continuously refine and evolve our value selling methodology by integrating customer feedback, market intelligence, and product evolution
• Serve as the primary conduit between sales teams and product—bringing back actionable feedback on AI use cases, objections, and adoption barriers
• Partner with product to shape roadmap priorities based on evolving buyer needs
• Champion internal use of Outreach AI across sales, success, and marketing teams
• Lead internal pilots to validate messaging and workflows before full-scale launches

Preferred Qualifications

• Are a seller at heart but strategic in approach
• Understand AI technology at an expert level in order to identify solutions using AI within the Outreach product
• Can speak both product and pipeline fluently
• Have strong intuition for what makes a sales team adopt, trust, and champion new technology

Benefits

• Flexible time off
• 401k to help you save for the future
• Generous medical, dental, and vision coverage for full-time employees and their dependents
• A parental leave program that includes options for a paid night nurse, and a gradual return to work
• Infertility/ assisted reproductive services benefit
• Employee referral bonuses to encourage the addition of great new people to the team
• Snacks and beverages in the Office, along with fun events to celebrate
• Diversity and inclusion programs that promote employee resource groups like Outreach Women's Network, Latinx community, Outreach Black Connection, AAPI community, Pride/LGBTQIA+, Gender+, Disability Community, and Veterans/Military