Strategic Program Director, Outreach
$150-200k
Sales execution platform
Be an early applicant
Sales execution platform
1001+ employees
Be an early applicant
$150-200k
1001+ employees
Company mission
To change the way companies engage with their customers throughout their lifecycle.
Role
Who you are
- This role is designed for a former management consultant with preferred operating experience in technology companies who thrives at the intersection of strategy and execution
- Someone who can ideate at the executive level, build a plan, orchestrate work streams across departments, and then personally drive it to completion
- Bachelor’s degree required; MBA or advanced business degree strongly preferred
- 12+ years Top-tier or boutique management consulting focused on technology, SaaS, AI, or digital transformation and/or
- Strategic operations, corporate strategy, Office of the CEO or Chief of Staff roles within a scaling technology company
- Proven track record of leading complex, cross-functional initiatives from strategy through execution
- History of successful relationships with visionary start up CEOs
- Direct experience working with C-suite leaders and presenting to executive and board audiences
- Experience in startup companies who are high-growth, fast-changing environments where priorities shift and ambiguity is constant
- Strategic & Tactical Execution: Can zoom out to enterprise strategy and zoom in to operational detail seamlessly
- Advanced Analytical Thinking: Expert in structured problem-solving, KPI design, and business case development
- Executive Communication: Exceptional ability to synthesize complexity into clear, compelling executive narratives
- Influence Without Authority: Trusted partner to senior leaders across functions. Works collaboratively to achieve desired outcomes
- Program & Operating Rigor: Brings structure, discipline, and momentum to ambiguous initiatives
- Judgment & Discretion: Trusted with highly sensitive leadership and company matters
- Bias for Action: Not just an advisor, personally accountable for results
- Thinker and doer with strong intellectual horsepower
- Comfortable with ambiguity, pace, and pressure
- Confident but humble; challenges ideas with data and respect
- Highly organized, detail-oriented, and outcomes-focused
- Energized by building, scaling, and transforming businesses
What the job involves
- Operating as a core member of the Office of the CEO, this individual will lead the company’s most critical, cross-functional initiatives from concept through execution, working directly with the Chief Executive Officer , Chief Business Officer and executive leadership team
- The Director of Strategic Programs is a highly analytical, execution-oriented leader responsible for turning enterprise strategy into measurable business outcomes
- This is a hands-on role for a strategic operator who is equally comfortable in models, board materials, working sessions, and execution trenches
- Lead CEO-sponsored, enterprise-wide strategic initiatives from problem definition through delivery and measurable impact
- Translate strategic priorities into structured programs with clear business cases, operating plans, milestones, owners, and KPIs
- Move fluidly between high-level strategy and day-to-day execution to ensure results, not just recommendations
- Partner effectively and closely with C-Suite level leaders to understand their current state of business and how potentially new directives may affect their current operations – eventually, be able to speak on their behalf with the CEO & CBO when new ideas or initiatives are brought to the table so that the first discussion is fruitful
- Lead rigorous quantitative and qualitative analysis on complex business problems (brand awareness, growth, churn, AI adoption, GTM efficiency, operating leverage, etc.)
- Build financial, operational, and scenario models to support executive decision-making
- Develop hypothesis-driven insights, pressure-test assumptions, and turn data into clear executive recommendations
- Drive execution across Sales, Marketing, Product, Engineering, Finance, People, and Customer Success
- Influence senior leaders without direct authority through structured problem-solving, clarity, trust, and credibility
- Identify risks, dependencies, and resource constraints early and actively remove roadblocks
- Be able to push new ideas that may not be popular by identifying how it could work for each C-Suite Leader (coming to the table with a solution versus a directive only)
- Act as a strategic extension of the Chief Executive Officer
- Collaborate in developing executive-level and board-ready materials including strategy narratives, program updates, operating reviews, KPI dashboards, and decision frameworks
- Support the Office of the CEO with strategic planning cycles, operating cadence reviews, transformation milestones, and executive offsites
- Give feedback to CEO on why ideas may or may not be worth pursuing by providing solid data and evidence, inclusive of considering financial and operational restrictions
- Establish disciplined operating rhythms, governance structures, and escalation paths for critical, cross—functional initiatives
- Track results against commitments with transparency and urgency
- Lead stakeholder communication and change management to ensure organizational alignment and adoption
Our take
Alongside the longstanding problems of identifying and closing sales, Customer Relationship Management (CRM) has long faced challenges with poorly integrated technology, which has inspired a flurry of companies targeting efficiency in the sector. Outreach is a sales execution platform that enables users to build more pipeline, proactively fix deal risks, and make the best decisions to advance their deals across every moment of the sales cycle.
Outreach is a leader in its category; delivering a comprehensive suite of sales tools, and generating AI-driven insights from a rich set of industry data. The company's focus on AI, which included the development of a ‘knowledge AI assistant’ for salespeople, is what allowed it to get ahead in the market. There are numerous competitors in the space, however Outreach has proved to command investor respect, having achieved Unicorn status in 2020.
Outreach has continued to display good growth, and has become a mission-critical part of the revenue stack for many customers - of which it boasts over 5000 globally. Notable names served by the company include Siemens, Twilio, and zoom.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-3% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Jun 2021
$200m
SERIES G
Jun 2020
$50m
SERIES F
Total funding: $527.3m
Company benefits
- Dental and vision coverage
- 401(K)
- Parental leave
- Flexible time off
- Work from home opportunities
- Health insurance
Company HQ
Interbay, Seattle, WA
Leadership
Manny Medina
(CEO)Manny was employee number three on Amazon’s AWS team, and led the Microsoft mobile division from launch.
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