When you spend more than two decades in digital marketing, you don’t just collect projects and clients. You collect scars. Campaigns that didn’t go as planned. Teams that broke under pressure. Budgets that vanished without clarity.
For Madhusudan Vasudev — or simply Maddy, as most call him — these scars became the foundation of a new kind of consulting practice: Ask Maddy.
Rather than building another agency or selling “one-size-fits-all” packages, Ask Maddy is built on a simple but powerful positioning:
“I am an outsider who works like an insider.”
Maddy works as a fractional Chief Digital Officer (CDO) / Chief Marketing Officer (CMO) — stepping into companies, agencies, and startups to bring clarity, structure, and senior-level digital leadership without the overhead of a full-time hire.
And in today’s messy digital ecosystem, that model is turning heads.
Why Founders Burn Money on Marketing
If you’ve been a founder, you’ve probably felt it. Marketing spend going out the door with very little to show for it.
Maddy has seen this firsthand, both inside agencies and as an advisor to business owners:
- Goals are unclear.
- Teams are overloaded or misaligned.
- Agencies promise the moon but deliver confusion.
- Delivery systems fail, even when campaigns succeed.
The result? Burnt budgets, frustrated founders, and growth that never compounds.
That’s where Ask Maddy steps in — not with more “services,” but with clarity.
What Ask Maddy Offers
At its core, Ask Maddy is about strategic leadership on demand. Here’s how it works:
1. Fractional CDO / CMO for Founders
Many businesses can’t justify a full-time digital leadership hire. But they desperately need strategic direction. Maddy fills that gap as a part-time senior leader who:
- Audits current marketing and tech spends.
- Aligns teams and agencies around real business goals.
- Builds delivery systems, SOPs, and workflows that actually scale.
2. Growth Advisory for Agencies
Agencies often get stuck in client delivery chaos. Maddy steps in as a fractional Chief Strategy Officer (CSO) to help:
- Define positioning.
- Build team workflows.
- Improve delivery systems and client trust.
3. Structure and Clarity for Scaling Businesses
Scaling businesses don’t just need leads; they need sanity. Ask Maddy helps brands build the systems and delivery engines that prevent growth from collapsing under its own weight.
👉 Explore the full offering here: Ask Maddy Website
Why Fractional Leadership Works
The concept of fractional leadership has been gaining momentum worldwide. Instead of hiring expensive executives full-time, founders bring in senior experts part-time or project-based.
The benefits are clear:
- Affordable senior perspective without overhead.
- Fresh eyes — outsiders who can spot problems internal teams can’t see.
- Flexibility — tap expertise when needed, pause when not.
Maddy’s unique edge? He’s not just a strategist. He’s a builder.
At Scrolling Rabbit, where he was brought in as a founding member in the driver’s seat, he built everything from scratch — workflows, hiring, delivery engines, and scale. That experience now powers his fractional model.
Two Decades, Many Lessons
Maddy’s journey spans some of the most respected digital agencies in India:
- 22feet Tribal Worldwide (DDB)
- KRDS
- Webenza
- Happy Creatives
Across these roles, he’s led strategy, delivery, and transformation for industries ranging from healthcare to education, from e-commerce to political campaigns.
The common thread? Influence, clarity, and scale.
That experience isn’t just theory. It’s been tested in the trenches — and those lessons now flow directly into Ask Maddy.
Why Clients Choose Ask Maddy
Here’s what sets Ask Maddy apart:
- Not another agency → No bloated teams, no hidden agendas.
- Not another consultant → Hands-on involvement, not just PowerPoints.
- Deep scars, clear perspective → Advice shaped by mistakes, not just successes.
- Custom structures, not cookie-cutter packages → Every engagement is tailored.
Freelance Platforms: Upwork and Guru
Ask Maddy isn’t just available through his own website. For founders and businesses that prefer trusted freelance ecosystems, Maddy actively maintains profiles on leading platforms:
- Upwork Profile: Maddy on Upwork
- Guru Profile: Maddy on Guru
These profiles make it easier for clients around the world to engage with him for project-based or retainer work, with the added credibility of third-party platforms.
Ask Maddy in Action: Common Scenarios
1. The Founder in Chaos
A D2C brand founder is burning lakhs every month on ads. Leads come in, but orders aren’t fulfilled on time. Customer trust dips.
Maddy steps in → audits delivery, builds systems, aligns teams. Ads stop being wasted fuel, and growth becomes sustainable.
2. The Agency That Can’t Scale
An agency is great at pitching, but terrible at delivery. Clients churn. Teams are demotivated.
Maddy steps in → creates delivery clarity, documentation, and accountability systems. Client retention rises, team morale improves, and revenue stabilises.
3. The Business That Needs Digital Direction
A traditional business knows digital is critical but doesn’t know where to start.
Maddy steps in → sets the roadmap, defines platforms, picks tools, and structures digital leadership. The business enters digital confidently instead of blindly.
SEO Optimisation and Visibility
For Desinema readers and Google searchers alike, the story of Ask Maddy ties into key themes trending today:
- Fractional CDO India
- Freelance CMO services
- Business advisory for founders
- Digital strategy for scaling startups
- Hire CDO on Upwork / Guru
By anchoring this piece with those keywords (naturally woven, not stuffed), the article can rank organically — ensuring founders, agencies, and even government organisations find it when searching for strategic clarity.
A Personal Note from Maddy
“I never set out to build another agency. After 20+ years in this space, what I realised is that most businesses don’t need more services. They need structure, clarity, and leadership that can connect the dots between strategy and execution. That’s what Ask Maddy is about. I’m not an outsider trying to sell. I work like an insider — but with the perspective of distance and scars.”
Final Word
In a world overflowing with agencies, consultants, and packaged solutions, Ask Maddy offers something rare — clarity backed by scars.
For founders who are burning money on marketing, agencies struggling to scale, or businesses lost in the digital maze, the answer may not be more spend or more noise. It may simply be to Ask Maddy.
👉 Explore: Ask Maddy Website
👉 Hire via Upwork: Maddy on Upwork
👉 Hire via Guru: Maddy on Guru
👉 Instagram:Instagram Ask Maddy
