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Oliver Armstrong
Smart Strategy. Flexible Leadership.
For Businesses
Leadership for Growth, Strategy and Innovation.
I figure out the market from the clients point of view, not just a cookie cutter template.
• Exited ML SaaS Founder
• VP Product at $20M+ ARR Scaleup
• Advisor to top-tier VC-backed startups
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core areas of expertise

What I Deliver:
On-Demand Executive Expertise

Turning strategy into momentum requires clarity, alignment, and the ability to execute at every level. These focus areas help teams move from vision to impact — with the right priorities, positioning, and processes in place.

• Strategic Roadmapping (90-day & 12-month horizons): Define priorities and align vision to execution.

• Innovation & AI Product Integration: Leverage emerging tech — LLMs, APIs — for new market advantages.

• Go-to-Market & Monetization: Refine positioning, drive adoption, and optimize revenue strategy.

• Product & Growth Leadership: Scale PLG and ready products for enterprise markets.

• Organizational Design & Enablement: Align teams and processes across product, engineering, and GTM.

• Board Narrative & Fundraising: Craft investor narratives and align strategy with funding goals.
core areas of expertise

What I Deliver:
On-Demand Executive Expertise

Turning strategy into momentum means making it actionable — with clear priorities, smart positioning, and aligned execution at every level.

I use my own Private AI tools and 20+ years of experience to work with 1st party data and research, delivering fast, tailored insights that drive real impact. Here’s where I add the most value:
Strategic Roadmapping (90-day & 12-month horizons)

Establish clear priorities and seamlessly bridge the gap between strategic vision and day-to-day execution, ensuring every action drives meaningful results.

Innovation & AI Product Integration

Unlock new market opportunities by harnessing cutting-edge technologies like large language models and APIs to drive smarter, faster innovation.

Go-to-Market & Monetization

Align your brand positioning with market needs, boost product adoption, and maximize revenue through data-driven strategy.

Product & Growth Leadership

Accelerate product-led growth and evolve your product strategy to confidently enter and thrive in enterprise markets.

Organizational Design & Enablement

Unify workflows and communication across product, engineering, and GTM functions to build momentum and scale with precision.

Board Narrative & Fundraising

Craft powerful and compelling investor narratives that not only articulate your unique vision and value proposition but also clearly demonstrate how your strategic roadmap is designed to attract, secure, and optimize funding — driving sustained growth and long-term success

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Had the privilege of working with Oliver when we funded his startup. He is driven, talented, and able to work across a number of dimensions, from product, to marketing, fundraising and sales. A strong founder, who would be an asset in any number of orgs and roles.
Jonah Midanik
Jonah Midanik, Managing Partner @ ForumVentures
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I have worked with Oliver on and off over the last 3 years. He's one of the best product leaders that I've worked with at a software business. He's a very quick learner and can quickly identify gaps in your business planning. His biggest strength is that he's incredible at creating a comprehensive strategic plan that can keep any product team closely aligned with the customer.

Mikhail Hutton
Mikhail Hutton, CEO @Candidus
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In just a few hours, Oliver uncovered key friction points in our acquisition and retention flow—his fixes drove immediate gains in growth.

JonCorrinXilo
Jon Corrin, CEO, Xilo.io
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Oliver delivered the candid, product leader’s reality check I needed—offering unique perspectives and unbiased insights that revealed blind spots, challenged my assumptions, and clarified where and how to attack the market.

Kevin Yang
Kevin Yang, Founder, instruc.ai
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Oliver helped MasterClass protect a marketing budget that scaled from $XX Million to $XXX Million over 3 years, preventing millions in wasted spend and giving our team peace of mind in a high-stakes environment.

Eric Clapper, MarTech @ MasterClass
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I met Oliver during our time at Forum Ventures, and he quickly became an invaluable sounding board. He was instrumental in helping Dataships secure our Seed Round—bringing clarity, connections, and the kind of founder-to-founder support that makes a real difference.

Michael Storan, Founder, dataships.io
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Oliver has been a trusted partner since our early startup days. As an angel investor in Brightback, he not only backed us personally but also introduced key investors who helped close a crucial bridge round—support that ultimately enabled our successful acquisition by Chargebee.

Guy Marion, Founder, brightback.com
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My CxO Role Breakdown -
A Versatile Executive Lens

CPO

Building the right product for the right user, in close partnership with Design, Engineering, and Marketing
Focus areas
Product vision
Roadmap
UX

CGO

Scaling user base and revenue through collaboration across Sales, Product, Pricing, and Business Development
Focus areas
Growth strategy
Revenue
Expansion

CSO

Shaping strategy and managing risk with CEO, Board, and Ops to ensure market fit and readiness
Focus areas
Long-term strategy
Risk
Positioning

CIO

Driving innovation by integrating emerging tech with R&D, Product, and Execs to stay ahead
focus areas
Innovation culture
Tech scouting

My Process

A clear, collaborative process designed to turn vision into execution. Deliverables Include:
Competitive Positioning Brief, GTM Playbooks, Product/Innovation, Audits, Strategic Playbook Presentation
Mikhail Hutton
"Elevated to industry leaders."
Step 1

Discovery & Audit

Analyze market, product, and internal landscape to uncover key insights and opportunities.
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Clear view of strengths and gaps
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Understanding of customer needs and market trends
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Insight into team and execution alignment
Step 2

Positioning & Competitive Strategy

Define a sharp, differentiated market position and competitive strategy.
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Clear product positioning and messaging
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Competitive landscape analysis
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Strategic narrative to guide marketing and sales
Step 3

Roadmap Development

Create actionable 90-day and 12-month roadmaps that turn strategy into execution.
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Prioritized product roadmap
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Aligned cross-functional goals
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Clear milestones and success metrics
Step 4

(Optional) Execution Partnership

Partner with teams to drive execution and maintain momentum.
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Ongoing product and GTM guidance
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Leadership alignment and team enablement
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Regular progress reviews and iteration
Pricing

Transparent Solutions, Tailored Prices

Explore our comprehensive pricing options designed to fit your needs. Customizable plans for every business stage.
Essentials Retainer
$12.5 K/month
Ideal for teams seeking strategic guidance and steady momentum without heavy involvement.
Features
Bi-weekly sessions
Roadmap & deliverable oversight
Ongoing async guidance between sessions
10 hours of specialized User Research, Architecture, Development, or Cyber Security consulting
Embedded Executive
 $18K–$25 K/month
Designed for high-growth teams needing hands-on, executive-level partnership and full strategic immersion.
Features
Weekly leadership sessions
Full roadmap & stakeholder alignment
Roadmap, product development, strategy
Go-to-market & cross-functional coordination
Clients

Who Do I work With

I’m a dedicated strategic partner who walks with companies through critical stages of growth and transformation.

I provide personalized guidance, deep expertise, and practical solutions to help you achieve lasting success.
Startups (Series A–C)

Bringing strategic maturity without adding C-suite headcount — shaping roadmaps, positioning, and growth.

SMBs in Growth Mode

Helping product and GTM teams realign and scale — building the foundation for the next stage of growth.

Organizations in Transition

Guiding companies through pivots, new funding rounds, or post-MVP acceleration — turning change into momentum.

FOR GROWING COMPANIES

Move Forward: With Clarity and Momentum

Build the right strategy, tell the right story, and turn ideas into impact.
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