JDO
CONSULTING
Transforming Technology Focused Firms to Greater Sales and Margin Growth
Growing Your Company Can Be a Challenge
Experience Makes the Difference
The Transition from Founder to CEO for Many Firms Can Be The Make or Break Step. Great CEOs Know When to Delegate and Expand Their Team, But There Can Be Challenges
Meet Jeffrey Osborn
Fractional CRO | CSO | Revenue Growth Strategist
With over 35 years of experience driving sales, profitability, and operational excellence, Jeffrey helps small to mid-sized technology products, services, and consulting companies scale revenue and margins through innovative sales and revenue transformation strategies. He has led global organizations with revenues up to $400M, helped scale profitable start-ups to over $50M, and advised venture capital, private equity, and early-stage investors on transformational strategies to drive hyper growth. Specializing in consultative sales and revenue operations, he aligns sales, marketing, and customer success to deliver sustainable, high-margin growth. His expertise spans SaaS, ITO, BPO, DaaS, and AI-powered solutions across industries like travel, retail, financial services, and high-tech.
As a trusted and proven fractional CRO/CSO, he leads organizations through transformative change, optimizing sales performance, accelerating deal velocity, and turning strategy into measurable results. Jeffrey’s established results are based on the following project goals for every client:
-
Aligns sales, marketing, and customer success to drive unified revenue growth
-
Develops and executes go-to-market strategies that accelerate pipeline and deal velocity
-
Optimizes pricing, positioning, and value propositions to improve win rates and margins
-
Builds high-performing, cross-functional revenue teams focused on execution and results
-
Drives strategic initiatives like market expansion, channel development, and upsell/cross-sell programs
Why Fractional Works For Many Companies
Proven Revenue Leadership
Without Full-Time Overhead
Unlock the power of proven revenue leadership without the cost of a full-time hire. Our fractional CRO services deliver executive-level strategy, structure, and sales acceleration tailored to your growth stage. Whether you're looking to scale faster, align go-to-market teams, or drive predictable revenue, we bring decades of experience to the table at a fraction of the cost and commitment.
Accelerated Time-to-Impact At a Lower Cost Point
Accelerate your time to impact with seasoned revenue leadership without the delay or expense of a full-time executive search. Our fractional CRO services plug in quickly to assess, align, and activate your go-to-market strategy, delivering results in weeks, not months. You get high-impact execution and strategic oversight from a proven leader, all at a lower cost and commitment than a full-time hire.
Flexibility to Match Business Needs
A fractional CRO gives growing companies the flexibility to scale revenue leadership as needs evolve. Whether you're entering a new market, building your first sales team, or refining your go-to-market motion, our on-demand expertise adapts to your stage and pace. You get executive-level guidance without locking into the cost or commitment of a full-time hire ensuring you stay agile while driving growth.
Flexible Service Models
CRO Strategy Session
(One Day)
Our one-day GTM and sales strategy session is designed to quickly identify and prioritize the biggest blockers to revenue growth. Through a focused workshop, we audit key pipeline deals, pressure-test your ICP, and deliver a short list of actions that unlock near-term results. Ideal for founders or sales leaders seeking clarity on where their sales process is stuck and how to fix it fast.
CRO Sprint
(30 Days)
The 30-day CRO Sprint is a tactical engagement built to generate fast wins and revenue clarity. We roll up our sleeves to triage stalled deals, tighten qualification, refine your ICP based on real buyer behavior, and align your sales and marketing motions. Clients leave with improved conversion rates, sharper GTM execution, and a clear path to predictable growth..
CRO Accelerator
(90 Days)
Our 90-day engagement delivers a full GTM reset designed to transform your revenue engine. We install a structured pipeline process, redesign your ICP to reflect product-market fit, launch expansion strategies for existing accounts, and establish sales leadership rhythms. It’s a fit for firms looking to turn inconsistent sales performance into a scalable, repeatable motion.
CRO Leadership (Ongoing)
For companies ready to scale, we offer a retained CRO service that embeds senior revenue leadership directly into your team. We take ownership of sales execution, forecast accuracy, and go-to-market alignment across sales, marketing, and customer success. Whether you need to land more logos, grow existing accounts, or build your GTM team, we deliver the roadmap and results.
How We Drive Results
Triage:
Unlock Immediate Revenue
We begin by immersing ourselves in your current go-to-market landscape to drive fast, measurable results. Our Triage phase focuses on closing late-stage deals, identifying untapped revenue within existing accounts, and rescuing at-risk clients facing pricing, competitive, or delivery issues. This hands-on, tactical engagement gives your sales team momentum, uncovers quick wins, and establishes a real-time view of where your revenue is leaking and where it can grow.
Transform:
Build Predictable Revenue
Once the immediate opportunities are stabilized, we shift into Transform — a phase focused on building scalable, repeatable revenue processes. We integrate insights from the field to redesign your sales motions, align cross-functional teams across marketing, product, services, and finance, and stand up the systems, playbooks, and enablement needed for consistency. The goal is to move from heroics to habits, establishing the foundation for sustainable growth and a fully aligned go-to-market engine.
Scale:
Accelerate Strategic Growth
With a solid operating foundation in place, we guide your business into the Scale phase — focused on accelerating long-term, strategic growth. This includes refining your ideal customer profile, expanding into new markets or verticals, optimizing GTM leadership, and building the forecasting and revenue intelligence needed for high-confidence scaling. Whether you're preparing for funding, acquisition, or category leadership, Scale ensures you have the structure and momentum to grow with precision.
Insights
In the journey of building a technology company, there comes a pivotal moment that often determines whether a promising startup will evolve into a thriving enterprise. This moment isn't marked by a funding round or product milestone, but by a founder's willingness to relinquish control over key operational functions.
Read the Full Blog Post on
Most technology ventures have to navigate the gap between their early private friends and family and angel rounds to reach the right revenue and growth to get into the game of professional capital. Many firms run out of funds or lack the right level of growth to get to this stage.
Read the Full Blog Post on
Growing technology companies often reach a critical inflection point where continued scaling is impossible due to an over-reliance on founders for closing deals. If your biggest deals still require the founder to jump in and save the sale, you haven't built a sales org; you’ve built a dependency.
Read the Full Blog Post on
Common Questions
