About

Jesse Weissman

Founder

Mission

Hello! I founded Crafted Digital Strategy to help you articulate and advance the future you envision: a new market to explore, a promising digital business strategy, or a project you know will make a tremendous difference. Finding your most valuable voice is about taking the time to research and reflect on how your idea positively impacts others. For over 20 years, I have created extraordinary business growth by helping executives and organizations find this voice and unlock the progress they deserve.

How We Work Together

Harvest the Data

This isn’t just about looking at data in spreadsheets. I’ll spend time with you researching what ground has already been covered, and depending on the project we may dive deeper into customer or market interviews, into troves of data piled in the corners of your company, or into the tangles of technology your company has purchased over the years.

Distill the Strategy

I like to explore the Customer’s “jobs-to-be-done” as a way to reduce complexity and focus on the most valuable qualities of an idea. And this is applicable whether we’re discussing ways to blend an App into an existing off-line experience, to build a profitable Data & Analytics team, or to align your company’s existing capabilities with a new market.

Craft a Plan

As an executive, I’ve hired countless firms with cookie-cutter methodologies to enable analytics and integrate data at scale. And that can be a great option for large global firms with endless time and resources. But I’ve also learned that the cookie crumbles in very expensive ways for companies that don’t fit this mold, perhaps because they’re smaller or simply due to the unique qualities of their business. As the name implies, Crafted Digital Strategy is for the innovative organization and executive who appreciates the benefits of custom design.

How I Can Help You

Executive Coaching

You have ideas that, so far, refuse to be held captive in writing. Perhaps you struggle to win or retain a seat at The Table of your organization. Or maybe it has been a while since you’ve needed to succinctly communicate your value proposition. We work together over 3-6 months to craft your most valuable voice. Examples could include an investment proposal for the C-Suite, building a business narrative from data, brainstorming a new idea, or refining your thought-leadership for publication.

Accelerator Project

As a founder or executive, you need help articulating the opportunity in a new market, or from a new digital/data product. Recent real-life examples include: assessing the go-to-market potential of The Blue Economy for a technology consultancy, and defining the digital product analytics/engagement strategy for a global fitness app + equipment company. Typical results (arriving in 3-6 months) include increased revenue, strategic clarity, process improvement and/or organizational alignment.

Fractional CDO

Realizing value from investments in data and analytics can be excruciatingly difficult, with failure rates approaching 80% not including employee burnout and costly inefficiency. I have over 25 years of leadership experience creating business growth from data, and building teams that endure. It’s a world filled with promising new ideas and technologies, but navigating the noise, complexity and complacency of an organization requires you to master your most valuable voice to be successful. With this option, I typically take a title in your company to craft and execute the digital strategy over 6 months – 2 years.

How I Work

I work either on a fixed-fee project basis or on retainer, depending on what we decide is the best way to accomplish your goals.

How to Learn More

I post 100% Organic (no AI) articles on this site, and my newsletter is published monthly. I encourage you to subscribe, and feel free to follow me on LinkedIn for real-time discussion.

How to Get Started

Reach out and schedule a call with me.

In our initial call we will discuss the idea(s) you want to advance, the circumstances of your business, and any challenges that impede your progress. The purpose of this call is to explore your objectives and the value created by achieving your goals. After this call, I will write a summarization of your needs and recommend a structure for our work together.

If we agree conceptually that our collaboration has a very high likelihood of generating substantial value, I will then send you a formal proposal which you’ll accept and then we can start working. I always manage my engagements to be able to take on new clients within a few weeks’ notice.

About Jesse

Jesse Weissman has over 25 years of leadership experience creating business growth from data by helping executives develop their busy employees, scattered data and bewildering technology into a symphonic experience that delights Customers and delivers solid returns.