Reporting to the Senior Manager, Enablement Curriculum and working across a cross-functional Enablement team, you'll build learning experiences that hold up in the field - objectives, practice, assessment, and the content that carries them. This is a builder's role. You'll decide how the learning actually works, and you'll own the quality of what ships. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. Who you are: An owner: You take pride in your outputs and their outcomes. You take ownership from design through launch and everything that comes after it. An innovator: You challenge the status quo, bring new ideas, and look for ways to improve what already exists. An agile problem solver: You shift seamlessly between detail and big picture to meet the moment, adapting to change with a solutions-oriented mindset. A lifelong learner: You challenge assumptions and use curiosity to drive continuous improvement. A trusted advisor: You ask sharp questions, synthesize complex ideas, and build relationships to understand and explain ambiguous concepts. A clear communicator: You bring structure, clarity and polish to your work - written, verbal or visual. What you’ll do: Build the curriculum for Global Commercial Customer Success. Develop high-quality enablement content (instructor-led materials, facilitator guides, eLearning, job aids and assessments) for both individual contributors and their frontline leaders, built to instructional design and adult learning principles. Build within the learner journey. Contribute to and build the components of role-specific journeys (onboarding, everboarding and on-demand) inside the curriculum arc for your area. Know what good looks like. Translate performance expectations into observable behaviors and clear proficiency standards. Turn
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Role overview
Job description
About Outreach
Outreach, founded in 2014, is the only complete agentic AI platform for revenue teams. Outreach infuses agentic AI, conversation intelligence, and assistive AI to power hundreds of use cases across revenue motions. From new logo prospecting to expansions, deal acceleration, driving retention, and forecasting, Outreach AI automates workflows and frees sellers to focus on more strategic conversations and actions. Revenue leaders benefit from connected account visibility, performance insights, and higher forecasting accuracy across every GTM team. World leading enterprise organizations use Outreach to power their revenue teams, including Databricks, SAP, Siemens, and Verizon to name a few.
About the Team
Our AI Advisors are where the promise of the platform becomes real for our customers. We act as trusted advisors — to our customers and to each other — partnering across Sales, Product, Marketing, and Professional Services as one team working toward the same outcome: customers who see measurable value and keep coming back for more. AI is part of how we get there — sharpening the insights we bring to every customer conversation. We lead with a customer-first mindset, take ownership of the results we commit to, and bring the curiosity to keep learning as the way our customers' work continues to evolve.
The Role
We're looking for a strategic, data-driven Senior AI GTM Advisor to partner with customers in maximizing value from our platform — leveraging AI to drive efficiency, adoption, and business outcomes. This role blends traditional CSM responsibilities with a strong focus on AI enablement, insights, and automation. AI is transforming how our customers operate, and this role makes sure they adopt it while they realize its full value, moving from manual processes to intelligent, automated workflows that drive real business impact.
Success in this role shows up in the numbers our customers and Outreach both care about; Net Revenue Retention, Gross Retention, and AI feature adoption; because when customers realize value, growth follows.
Your Daily Adventures
Own a portfolio of customers and ensure they achieve measurable business outcomes
Drive adoption of core platform capabilities, with a focus on AI-powered features and credit consumption
Lead Executive Business Reviews (EBRs) tied to ROI, productivity gains, and revenue impact
Educate customers on AI capabilities (e.g., automation, predictive insights, personalization)
Own credit consumption as a primary, accountable metric for their book of named accounts
Define and prioritize AI use cases with the customer — translating a customer's GTM motion (prospecting, pipeline management, forecasting, coaching) into a sequenced roadmap of Amplify agent use cases that drives sustained adoption.
Lead hands-on change management with sellers and revenue leaders — running enablement sessions, coaching frontline adoption habits, and working with customer managers so the platform is adopted
Act as a strategist and influencer on the customer's AI GTM strategy — shaping how and where AI agents get embedded into the customer's sales process, and helping to build the internal business case for expanding usage into new teams and workflows
Leverage customer data and AI insights to proactively identify risks and expansion opportunities
Monitor health scores, usage trends, and engagement signals to drive action
Use AI tools to surface recommendations and next best actions
Own renewal strategy and mitigate churn/contraction risk
Identify and drive expansion opportunities (upsell/cross-sell), especially tied to AI value
Partner with Sales and RevOps to align on account strategy
Represent the voice of the customer back into Product and Marketing, particularly on agent performance, prompt quality, and adoption friction
Partner with Professional Services on onboarding and complex implementations
Provide feedback on AI models, accuracy, and customer sentiment
Our Vision of You
5+ years in Customer Success, Account Management, GTM/RevOps, Consulting, or a sales-process/technology advisory role, ideally at a SaaS company with complex, multi-product, AI-enabled offerings
Demonstrated experience driving software or platform adoption and leading change management with sellers and frontline sales managers
Strong executive presence and the ability to influence VP/C-level stakeholders on AI GTM strategy and organizational change, not just product usage
Comfort working with AI/agent-based products and translating technical capability into business outcomes for non-technical stakeholders
Experience managing enterprise customer relationships
Strong analytical mindset with the ability to interpret data and translate into action
Proven track record of driving renewals, expansion, and customer outcomes
Strategic thinking and consultative problem-solving mindset
Experience working with AI/ML-powered products or automation tools
Familiarity with concepts like predictive analytics, generative AI, or workflow automation
Working knowledge of core GTM workflows — inbound and outbound prospecting, pipeline management, retain/expand motions, forecasting, and manager coaching cadences — along with familiarity operating alongside the personas who own them (CROs, VPs of Sales, frontline sales managers, RevOps, and CSMs)
Working knowledge of how to create prompts and consistent use of tools like Claude, Gemini, etc.
Experience using platforms like Salesforce, Gainsight, or Outreach
Curiosity and adaptability in a fast-evolving AI landscape
Risk management and mitigation planning experience
#LI-LT
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.
Customer Outcomes & Value Realization
AI Adoption & Enablement
Data-Driven Account Management
Retention & Growth
Cross-Functional Collaboration
Required Qualifications
Preferred Qualifications (AI-Focused)
About this listing
- Listed from Outreach's careers site via Lever · last confirmed on the source 19 Oct 2026
- Posted 29 Jul 2026
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What they are looking for
Skills & requirements
Department · Customer Success
Hiring company
Outreach
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