Quick WINs: Greg Schaffer WINs by focusing on service!

Quick WINs: Greg Schaffer WINs by focusing on service!

By Ian Richardson, Managing Partner, Richardson & Richardson Consulting

Podcast Season 1, Episode 17 Guest: Greg Schaffer, CEO, vCISO Services LLC

Greg Schaffer is the founder of vCISO Services, LLC, launched in 2017 to combat the growing threat of cyber-attacks to SMBs with part-time seasoned executive information security expertise at a fraction of the cost of hiring a full-time CISO.

He has over 33 years of experience in information technology and security including over 15 years at the CISO level. Before launching vCISO Services, LLC, He served as the senior information security executive in higher education for the largest undergraduate university in Tennessee, in government for the largest city in Tennessee, and in finance for the third largest Tennessee-headquartered bank. He is passionate about information security both within the job and in external endeavors, having participated and volunteered in leadership positions in several information security organizations, local and national.

This passion has prompted him to pursue other information security projects to help SMBs. He produces and host the Virtual CISO Moment podcast (https://open.spotify.com/show/3A9PI9NlmBbSKAhHGivspV) and have authored Information Security for Small and Midsized Businesses (https://www.amazon.com/Information-Security-Small-Midsized-Businesses-ebook/dp/B08WKQ9PBJ/).

Our conversation was awesome and engaging and focused on the topics of what customers “need” versus “want”, balancing growth against stability, and finding your passion. As always, I took notes on the conversations, and I have those notes here for your reference and use as you see fit.

  1. Needs vs. Wants: There is an age old saying of “the customer is always right” that doesn’t ring quite true in complex service engagements. I.T., and especially cyber security, is never something that someone “wants.” In today’s environment, they always fall under the “need” category. Being able to navigate the complex, awkward, and uncomfortable conversations around those needs is something that Greg and his team focus on. Using proper discovery techniques, as well as making sure to explain things simple and straightforward, aligning to customer needs and pains, hopes, and beliefs is critical to any modern consultative sales organization.
  2. Growth vs. Stability: Balancing the natural desire to “ride the hurricane” of rapid yet uncontrolled growth against having a sane and stable business that might not grow as fast as you want is a difficult task. Greg has a straightforward approach that targets a reasonable growth target while saying “no” to opportunities that aren’t a proper fit for the organization, including those of partnerships and clients. I appreciated his focus on making sure the business’ health comes first, even over extra revenue.
  3. Finding your Passion: Greg has a great founder story around being called to service, even when he could have safely stayed in a comfortable position and career. That calling for “more” struck home with me and reflected my own story of diving into R&R versus staying in a comfortable, but un-fulfilling, position at my old I.T. firm. Taking the risk to carve out your legacy is something every entrepreneur should heavily evaluate – after all, we only live once.

I gain so much value from meeting with fellow entrepreneurs and leaders. Each and every person I speak with brings their own experiences, knowledge, and viewpoints to the table, and without fail, I walk away with a head full of ideas and motivation to do better in my own business. I so greatly appreciate NAMES willingness to come onto W.I.N. and share PRONOUN story.

If you’re interested in joining me on an episode of W.I.N., it would be my privilege to host you. You can book your spot by visiting https://randr.consulting/connect and selecting the Podcast Booking option from the services menu. You can find previous episodes of W.I.N. on our website and subscribe to it on whatever your platform of choice is.

Always Forward,


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