Head of AI Value Strategy

About Outreach

Outreach, founded in 2014, is the only complete AI Revenue Workflow Platform that helps sales leaders benefit from connected account visibility, performance insights, and higher forecasting accuracy across every GTM team. Outreach infuses agentic AI to power 100s of use cases across sales motions. From new logo prospecting to renewal and expansion, Outreach AI automates workflows and frees sellers to focus on more strategic conversations and actions. Global organizations use Outreach to power their revenue teams, including SAP, Siemens, Snowflake, ZoomInfo, and Verizon to name a few. To learn more, please visit www.outreach.io.

About the Role:

Reporting to the Chief Revenue Officer, the Head of AI Value Strategy will be responsible for meeting with C-Suite industry leaders to uncover their pain points and deliver strategy and solutions using Outreach’s platform, specifically our AI functionality.This role will work with some of the most forward-thinking company leaders in the world and play a key customer facing role in scaling how we position and sell our product. This role will also play a key role in educating our sales team as a whole on how to sell AI products with an emphasis on value outcomes.  

Ideal candidates bring a background in AI development/engineering, sales engineering, sales management, value consulting or revenue strategy, and can credibly speak to top company leaders in varying industries. Candidates must understand not just how AI works—but how to educate the market, sell it, defend it, and operationalize it in high-stakes sales cycles. Top candidates will understand how AI and specifically Outreach’s product can solve real world business problems.  

Location: Open to remote within the US.

• GTM Strategy & Execution 
• 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. 
• Sales Leadership & Field Enablement 
• 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. 
• Competitive Differentiation 
• 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. 
• Performance & Value Impact 
• 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. 
• Voice of Field & Customer 
• 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. 

• 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. 
• You’ll Succeed in This Role If You… 
• 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. 

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Why You’ll Love It Here

• 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

Outreach is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

Our success is reliant on building teams that include people from different backgrounds and experiences who can elevate assumptions and ideas with fresh perspectives. We're dedicated to hiring the whole human, not just a resume. To that end, we look for a diverse pool of applicants-including those from historically marginalized groups. We would like to invite you to apply even if you don't think you meet all of the requirements listed below. We don't want a few lines in a job description to get between us and the opportunity to meet you.