Helping Organizations Stop Solving the Wrong Problems
MARKETING EXECUTIVE, RISK THINKER, STARTUP MENTOR
Scott Fenstermaker is a Chicago-based marketing executive, author, speaker, and Vice President of Digital Marketing at Riskonnect.
He writes and speaks about hidden risk, organizational blind spots, and the marketing mistakes that keep teams from growing.
Hi, I’m Scott. I’ve built a career talking people out of solving the wrong problems.
At Riskonnect, I lead digital marketing and build demand generation and thought leadership programs for the risk management space. I also host Risk@Work, an educational series featuring conversations with enterprise risk leaders, analysts, and practitioners.
Outside of Riskonnect, I mentor startup founders at 1871, Chicago’s world-ranked business incubator, where I help early-stage companies diagnose the strategic and marketing blind spots that can keep them from scaling.
I research and write on hidden systemic risk, organizational fragility, and why companies often fail to see the risks inside their own systems. I’ve written The Intelligent Content Playbook for fellow digital marketers and The Hunt for Hidden Risks for risk practitioners.
- 2020: With the Riskonnect digital team, I created the Risk@Work web series, a forum for risk professionals to learn from the industry’s most respected thought leaders. In response to the COVID-19 pandemic, we were first to market with recovery-related thought leadership, culminating in the Recovery@Riskonnect recovery microsite. Despite the pandemic year, we increased captured leads by +68.2% over 2019, web traffic by +10.4%, and social media growth by +140%.
- 2019: After joining as Digital Director of Riskonnect, I led a complete redesign of the company’s website and social presence. The initiative improved metrics in traffic, engagement and form conversions. My digital team surpassed targets for MQLs (104%), site visitors (195%) and social media growth (121%).
- 2018: At PowerPost, I created the “Brand Publishing Masterclass,” the first-of-its-kind expert-level webinar forum for content marketers could learn from the industry’s most cutting-edge, counterintuitive speakers and thought leaders.
- 2017: After the PowerPost acquisition I was made Vice President of Marketing. I directed the organization’s lead generation strategy, and oversee marketing strategy for our clients.
- 2016: While at SocialMediaBeast, I lead the agency’s performance-based digital advertising, marketing automation and SEO. I managed an annual client paid media portfolio of $2 million, achieving benchmark KPIs for clients.
- 2012: At Systat Software, I built up the recently relaunched SYSTAT product revenue from zero to $700,000 per year in under two years; produced over 150 qualified sales leads per week in the target market.
- I am a proud Business Mentor at the 1871 business incubator located at the Merchandise Mart.
- I teach programs on marketing analytics and antifragility for the 1871 PYROS program for founders. Check out my speaking programs here.
- The secret to a really successful marketing operation is to create an environment where young marketers are constantly learning with excellent coaching and guidance. Team morale can remain high even through adverse times if team members can see that they’re developing crucial skills.

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The Intelligent Content Playbook is an eBook that distills the best content creation strategies and optimization techniques from the industry’s top marketers.Inspired by Tim Ferriss’ Tools of Titans, the book collects and refines the best practices from guest instructors featured in PowerPost’s ‘Brand Publishing Masterclass.’ |
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- Michael Brenner, CEO of the Marketing Insider Group
- Adele Revella, author and CEO of The Buyer Persona Institute
- Park Howell, Founder of The Business of Story
- Michele Linn, Co-Founder of Mantis Research
- Mike Kaput, Director of Marketing Artificial Intelligence Institute
- Shane Barker of Shane Barker Consulting
- Julia McCoy, CEO of Express Writers
- Chris Penn, CEO and Founder of BrainTrust Insights
EXPERTISE
Digital Marketing Strategy
Building digital programs that connect positioning, demand generation, content, search, analytics, and conversion.
Risk and Thought Leadership
Translating complex ideas in enterprise risk, resilience, and organizational blind spots into clear, useful content.
Startup Mentoring
Helping founders avoid premature marketing spend by working backward to product strategy, positioning, and customer clarity.
Content and Demand Generation
Creating educational programs, campaigns, and resources that help complex B2B audiences understand what matters.
Speaking and Workshops
Teaching audiences how to diagnose the real problem before investing time, budget, and attention in the wrong solution.
Antifragility Techniques
Applying systemic risk theory to organizations themselves, creating operations and departments that strengthen from stressors.
DIGITAL MARKETING PORTFOLIO
SPEAKING AND TEACHING
Do you need an entertaining, informative marketing speaker for your next event?
I have appeared at numerous marketing panels and keynoted for several Chicagoland industry associations. He delivers presentations densely packed with actionable tips that audiences can take back and use immediately.
Please click here to learn more about topics and availability.

LELAND WILKINSONChief Scientist, H2O.ai
JOHN BURKEEnterprise Sales, TMA Systems
