A reporter recently asked for my IT-related career advice as it relates to outsourced digital marketing. I've been working in and around the IT industry since 1990.

Early on in my career, most of my IT roles were traditional IT jobs -- help desk / PC support specialist, business unit technologist, trainer, and system engineer -- as well as working as an outsourced CIO for small businesses with no or limited in-house IT. 

As an early adopter of Windows, I was one of the first 30,000 MCSEs (Microsoft Certified System Engineers) worldwide when I got certified back in 1997.

Outsourced Digital Marketing for Tech Startups and Scaleups

Since 2002, I've worked as outsourced digital marketing for IT companies -- typically IaaS, SaaS, and Fintech startups. And I am 28x certified by HubSpot Academy, including in Inbound Marketing, Content Marketing, Digital Advertising, Email Marketing, Social Media Marketing, and Sales Enablement.

I’m a former Microsoft Corporation content provider for and an advisor to the Small Business Server (SBS) product teams and small business channel partner teams in Redmond, Washington.

I’ve led marketing for a venture-based B2B SaaS company that’s applying AI in the accounting and enterprise finance space.

With a deep specialization in the SaaS, cloud services, data center, and hosting industries, I’ve presented educational sessions at MSP EXPO/IT EXPO, HostingCon, Data Center World, and DatacenterDynamics.

I began my career marketing and selling higher education PC hardware and software solutions for IBM Academic Information Systems (ACIS) and supported high-leverage co-marketing campaigns.

Job Title

Digital Transformation, Go-to-Market Content Strategist

(for Mid-Market and Enterprise IaaS, SaaS, and Fintech)

What Does a Typical Day Look Like? (A Day in the Life)

I lead workshops with clients -- typically CEOs of tech startups -- looking to attract, engage and delight more of the right kinds of clients to hit their company's growth targets.

I meet with internal and external team members that help our clients implement these growth plans around digital marketing and sales enablement.

I also head up my own company's thought leadership publishing.

For college students exploring this kind of career path, I'd recommend that you seek out paid internships and meaningful part-time jobs during college in digital marketing roles for B2B technology companies that invest aggressively in content marketing.

Pros and Cons of a Career in Outsourced Digital Marketing


  • Always learning about new technologies to help IT clients build awareness in the marketplace

  • Always learning about the latest advancements in marketing technology and sales technology to help IT clients stay competitive in their go-to-market strategy


  • There are a lot of toxic workplace cultures that set companies up to fail on digital transformation initiatives. (The combination of ignorance + arrogance is rampant in many that are supposed to be leading the charge on all things digital.)

  • Finding IT companies and leadership teams that are truly committed to building a brand that's differentiated, using thought leadership as assets/leverage, building self-awareness about competitive marketplace realities, investing in customer insight that allows them to sell to and service customers the way their customers want to buy, and prioritizing growth.

Are you contemplating a career in outsourced digital marketing? If so, what questions do you have? Let me know in the comments.


And if you're looking to launch your own outsourced digital marketing firm that works with B2B SaaS clients, enroll now in our free 7-day eCourse: Go-to-Market Strategy 101 for B2B SaaS Startups and Scaleups.

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