Always a Winger: People Person and Unapologetic Marketer with Amy Lewis (1/2)

Nerd Journey: Career Advice for the Technology Professional

Who knew leaving publishing might result in a career as a marketer in the tech industry? Amy Lewis was encouraged to pursue a role at Cisco by a career counselor who recognized her unique strengths. Now Amy refers to herself as an unapologetic marketer and a people person. On the soccer field and in her career, she is always a winger. She is focused more on the assist than scoring the goal.

In episode 301, Amy shares her early career transition from publishing to marketing for Cisco. We’ll discuss what storytelling is and how it can be used with individuals or large groups of people and how product marketing is about finding connective tissue. Amy also weighs in on online marketing, why she enjoys it, and how she learned to communicate with executives. Listen closely to learn about the impact of having good mentors throughout a career.

Original Recording Date: 09-19-2024

Topics – An Intentional Career Change, People Person and Unapologetic Marketer, Social Aspects of Marketing and Storytelling, Skills and Personas, Product Marketing as Connective Tissue, Candid Headlines and Communicating with Executives, Becoming the Interviewer

2:03 – An Intentional Career Change

• Amy Lewis is the director of enterprise marketing at GitHub.
  • She is also known as @CommsNinja.
• Amy tells us she majored in English and Political Science in school. After a 10-year career in publishing, she wanted to try a new career and landed in technology.
  • “Greatly oversimplified, it started with a Commodore 64, and then we wound up here.” – Amy Lewis
• Has the background in English and Political Science been an advantage since Amy got into the tech industry (i.e. experience in multiple different types of marketing roles)?
  • Amy says yes and went to a career counselor at the time she wanted to make a career change out of publishing.
  • “You have a really interesting skill set. You’re a storyteller, but you understand technology. You see where the world is going…. Cisco needs people like you. Technology needs people like you, people who can tell stories…. Go get a job there.” – Amy Lewis, feedback she received from a career counselor right before she joined Cisco
  • Amy tells us no one in her family worked in technology, and she had no contacts in technology. But after blind applying, she landed a role at Cisco.
  • Amy leaned into storytelling and making complex things simpler and understandable for others.
  • She did not know certain skills would be so applicable in this kind of career change, but she made the pivot at the suggestion of the career counselor.
  • Thinking back, Amy doesn’t remember how she found the career counselor originally.
• What made Amy want to leave publishing as a career?
  • Amy has been thinking a lot lately about return to office (or RTO as we might call it) because she has been working remotely for many years. She worked in New York at the company headquarters and then would later move away to start a family and work remotely.
    • Amy cites some advice from her mentor Brian Gracely about career limitations when you do not work in the same location as a company’s headquarters.
    • While working remotely for the publishing company, Amy saw a number of people get promoted. She felt at the publisher she would not be able to climb or grow any longer and that a new challenge was needed. It seems like she in many ways was out of new things to learn.
    • During the time Amy worked for the publisher, AWS was still Amazon.
  • At the remote office where Amy worked for the publisher, she was in charge of the server closet. In addition to this, Amy had digitized a number of properties for the publisher.
• Did leveling up mean becoming a manager, increasing salary, becoming a team lead, or just taking on new responsibilities?
  • Amy tells us it was all of these things. She is a competitive person.
  • Amy already had children, knew she did not want to have any more, and felt she could take more chances.
    • Amy needed to be with a stable company that would not fire her while on maternity leave. This is important for any working woman out there, even if left unstated.
    • Amy knew she could get paid more. She also had a director title but could not manage people because she worked remotely.
    • “I was ready to try something new, so I kind of restarted everything…. I’m ten years in. I’ve got a lot of contacts, connections, comfort. I had and raised my kids kind of in that environment, and I chucked it all away and…took a temp to perm contractor role at Cisco to get my foot in the door and try something new.” – Amy Lewis

8:39 – People Person and Unapologetic Marketer

• How was Amy’s previous experience looked at coming into the temp role at Cisco?
  • Amy started working as part of a content syndication program, which was focused on storytelling. At the time she hit all the right keywords for the role and was going to outpace most everyone else because of her experience.
  • After building websites and digital properties at the publishing company, Amy knew the disciplines of content syndication and online marketing well. These areas became her initial focus as part of the role at Cisco.
  • Amy describes herself then as someone “not afraid of the server closet and familiar with content.”
  • John highlights that Amy was the exact combination of things her employer was looking for at the time (what we might call a unicorn).
  • “This is the story of me, but everybody is a unicorn. Everybody’s got a superpower. Everybody’s got something that makes them unique. People say this, and when you forget it, let us all be reminded. Figure out who you are, what you’re good at, what drives you, and best of all, if what drives you is also good for business…and then be unapologetic about it and do it over and over and over again. Because I can either be half as good as somebody else if I’m trying to pretend to be them. Or I can be the very best Amy Lewis in the world.” – Amy Lewis
    • Amy embraced her unique skill set to excel in all of her previous roles and continued to embrace it when she landed at Cisco.
  • “I’m a people person. I call myself an unapologetic marketer…. In a traditional publishing company, it was weird to be a marketer there. And in tech, it can feel weird to be a marketer…” – Amy Lewis
  • In the publishing industry, Amy built the online marketing department and helped with the website. She worked for a small company and had easy access to the business owner.
    • As a storyteller, Amy finds connection in things that on the surface do not seem connected.
    • Even before Twitter, Amy would connect with people using online bulletin boards like phpBB.
  • Amy knows she is uniquely good at watching, listening to people, understanding personas / specific groups of people (i.e. the audience), and turning it into something using her creativity.
    • Amy continues to focus on what she is good at, what she likes, and how it serves the business – the connective tissue.
    • Amy mentioned her company once sold page-a-day calendars to the cat buying audience.
    • “Honestly, a cat lady is as passionate as somebody is about the type of phone they have in their pocket is as passionate about the type of networking gear that they use is as passionate about the software stack they’re engaged with. People are passionate, and it’s about people. I’m a people person.” – Amy Lewis
• Was marketing something Amy learned in school or picked up on the job?
  • Many people who are now in marketing had early interests in cults, serial killers, and other dark things. Amy’s field of study required reading all kinds of books on political movements, etc. (which is really marketing).
  • Amy mentioned marketers naturally seem to want to know what makes people tick. For her, it’s a combination of technology, how the world works, and natural curiosity.
  • John cites recent political cycles that are a merging of political movement and online audience building. Even before the internet, building a social movement was a form of marketing. It was about going to meet people, networking with them, connecting around an idea, and building community.
    • Amy’s example is one of reading about these types of movements and then applying that knowledge in a new area.
  • Amy’s mother was an English teacher

17:02 – Social Aspects of Marketing and Storytelling

• Was Amy interested in conversations with other people from a young age or ensuring she could collaborate with others in her work? What about that social aspect of working in marketing?
  • Amy started as a Chemistry major but realized she didn’t want to be stuck in a lab.
  • “I don’t want that. I want to be front of the house. And I don’t know that I wanted to be on a stage per se, but I knew I didn’t want to be in a lab…just doing lab things.” – Amy Lewis, on the decision to not keep pursuing Chemistry
  • Amy even thought about being a lawyer, especially since she had experience as a debater in high school and college, but that did not seem right.
  • “The other kind of spoiler alert is I’m an introvert. I may seem extraverted, but I think I shine a lot brighter online…. I can decompress. I can be behind my keyboard. I can go read a book afterward….I think there’s a lot of us like that too.” – Amy Lewis
  • Amy remembers a study that claimed more marketers were introverts as opposed to extroverts. Marketers like to observe their surroundings and do pattern recognition from there.
• We may have jumped to the conclusion that storytelling and people a people person necessitates being a 1-1 type of person. Is storytelling more of a broadcast or one to many type of communication?
  • Amy thinks people in sales might do better in the 1-1 communication or extraverted world as she calls it.
  • Marketers need to be able to make you feel like it’s 1-to-1, 1-to-few, and then 1-to-many or 1-to-masses. Amy has operated at each level without realizing it.
  • “I understand how to take people’s interest and passion and connect them with each other into that passion. And that I can apply to a lot of different things.” – Amy Lewis
    • Amy has done this with cake mixes and barbecue to bacon and datacenters.
  • Amy likes to take a lot of 1-to-1 observations and consider how much of it is true for 1-to-many and 1-to-masses. Is it connective tissue on a topic?
  • Amy says the best thing about working in technology is the constant new set of ideas, connecting people to these ideas, and then connecting them to each other.
• Nick says in this way the eyes are on Amy’s content or her ideas and not necessarily on her like she’s on stage.
  • Amy is a late-in-life football player (i.e. soccer), and one of her kids is the goalkeeper. You might think Amy would naturally gravitate to being a striker, but she enjoys being a winger.
  • “But the longer I play, the more I enjoy being a winger. And it’s so much less about how many goals I score than my assists. That’s the count that I keep in my head on the field. And I think that speaks a lot to my personality. To your point, I like the stories to shine. And I talk a lot about the invisible hand and how do you connect people to things? I don’t have to stand in front of it all the time, and I have found the longer I’m in career the more I really enjoy leading teams, setting people up for success, and…setting the idea up for success.” – Amy Lewis

22:49 – Skills and Personas

• Nick thinks we can see some of our own skills but will also need help seeing some of them, just like when Amy went to see the career counselor.
  • “I’ve often said, if you want to know what you’re good at or what your reputation is, turn and ask the person next to you. It is unbelievable how quick it will be. They will know. Just say, ‘what’s one word that you think when you think about me?’ Other people know what we’re known for before we do.” – Amy Lewis
  • Amy has done mentoring throughout her career. She spent 5 years as part of The Geek Whisperers and thinking about careers and has done a lot of mentoring in addition to that.
    • Amy likes to observe people in a setting and offer feedback on their strengths and qualities. She reminds us that this kind of feedback is a gift, and we often forget to ask for it.
    • Going back to the soccer analogy, Amy doesn’t know if the goals will always come, but she can always provide someone else a pass.
  • Does it seem narcissistic to ask someone for this kind of feedback?
    • “I like to catch people being great at something. Because they often don’t know, or if they do, it sure feels good to have somebody see it.” – Amy Lewis
  • Amy describes a project she did with the team at Dick’s Sporting Goods. Amy took this role at Dick’s Sporting Goods during a time when she was trying to choose between going back to working for a company she really loved and trying something completely different.
    • A mentor of Amy’s encouraged her to take the role at Dick’s, and she followed the advice, eventually building out a team.
    • Amy’s team worked within the Office of the CTO, which previously did not exist.
    • After observing and working with her team for a while, Amy built a slide deck and gave everyone a superpower and a superhero name. The gift Amy’s team gave her back was dubbing her the analogizer. This fits Amy’s method of storytelling – using analogies to “feel” the story and make it relatable.
    • John describes one of the best teachers he had in school and that teacher’s ability to restate the lesson he wanted to teach in the language of the hobby or sport based on a person’s interest. John has tried to emulate this style over the course of his career.
• Amy has been thinking a great deal about personas lately.
  • We live in a world where we know social media can feed our confirmation biases.
  • When marketers do their job well, they do it to serve a persona.
  • “It’s treating people with respect. It’s hearing them. It’s seeing them. It’s asking the question…all those tactics to either by observation or by direct question to get to know somebody and then to land what you’re trying to say. And then, to meet them halfway.” – Amy Lewis, on the marketer’s role serving personas
  • We talk about the difference between poor and excellent communicators with excellent communicators coming as far or as close to someone to help close the gap.
    • When communicating with someone and having a disagreement, consider whether you want to be right or you want to stay married. Either choice is a choice.
    • Amy highlights the importance of communication to close gaps and truly understand a persona.
• John highlights internet marketing as being focused on 1-to-masses and can lead to recency bias. Audience categorization can be difficult.
  • Amy says this really takes work, and we need to remember what we see in our social media feeds are likely not the same as what others see.
  • “If we don’t actively seek a difference of opinion, you’ll never figure out how to close the gap. You’ll only know how to close the gap with someone who thinks and looks and sounds just like you. And I think we all have to work at finding many voices and listening and thinking about our own to offset that recency.” – Amy Lewis
  • Amy mentions the emphasis in schools on citation and original content. The education we got is very different than what children are getting now.
  • Amy suggests we are raising a generation that is more critical, a group who is aware they are getting recency bias from being inside “the system.” That makes for an interesting group to market to and with.
  • John shares a story about the perception of typing as a necessary skill and compares it to the necessity presently to be able to use presentation software (PowerPoint, Google Slides) or understand sentiment from groups through social media.

33:15 – Product Marketing as Connective Tissue

• Amy likes to understand where groups can align and the connective tissue between them.
  • “Product marketing in some ways is no more than figuring that out…what your value props are and how they connect…to people’s beliefs and needs. That’s what it is. It’s messaging a positioning and then timing.” – Amy Lewis
• John wonders if product marketing is intentionally filled with jargon to foster the feeling of an in crowd who understands the jargon?
  • Amy says yes and calls it a tool often used. We discuss “othering” and “inning” in relation to this.
  • This likely becomes clearer when looking at commercial marketing where things like toothpaste say something about a personality.
  • A product marketer has a bag of tricks. They want to ensure they use product truth and build the messaging in a way that makes people feel they are smarter, ahead of the curve, etc.
  • “It can be true and work at the same time.” – Amy Lewis, on product marketing
• Does product marketing fit within a product team or in its own marketing funnel within an organization?
  • Amy mentions attending ad speaking at a Product Marketing Alliance conference recently.
  • Someone did a presentation sharing the various titles you can find in product marketing, and it made Amy think about how product marketing can take so many forms. Here’s how she thinks about it:
    • Within technology specifically, there is a broad group that is corporate marketing and a broad group that is product marketing.
    • Product marketing is like a slider bar starting with the product and its specifics and then getting more technical. From there corporate marketing would be more generalized information for the masses such as things that demonstrate thought leadership.
    • Someone passionate about the product and the details may gravitate more toward technical marketing or technical product marketing over general product marketing.
    • Many companies organize based on this principle, and it’s important to have both skill sets. On one end you have deep technical details of a product and working with product management and on the other more thought leadership (and a lot in between).
    • Events marketing, for example, would probably be filed under corporate marketing usually.
    • Corporate marketing has to be somewhat neutral, whereas product marketing will sit inside a business unit or division. Usually field marketing, communications, event marketing, etc. fit within the broader corporate marketing area.
    • In companies with a CMO (Chief Marketing Officer), communications usually will be for both internal and external, which includes public relations.
    • There are probably slight variations on all of the above (i.e. field marketing may be field embedded, etc.).
  • At the conference Amy met so many people across so many industries, and they all had the same complaints and problems.
    • For Amy, it was amazing to meet these people and listen to their stories. This helped to combat some of the confirmation biases we discussed earlier.

40:21 – Candid Headlines and Communicating with Executives

• Our discussion returns back to Amy’s temp to hire role at Cisco.
• Amy talks about this as being a moment in her career. Someone helped turn her badge from red to blue (i.e. full-time).
  • As a contractor, Amy was running a specific program and needed to present at a MBR (monthly business review). This is similar to a QBR (quarterly business review).
  • At the time, Amy was running a program but wasn’t getting the resources needed despite her attempts. Things were not going well.
  • “Either we get resourced and we change this, this, and this…or you should just cu the program. This is not a good use of resources.” – Amy Lewis, reporting the status of a program she was running to stakeholders in an honest and direct way
  • This was Amy’s program and had her name attached to it. She was hired almost on the spot.
  • Some of the other presenters were not sharing the true story of how their programs were going. Amy calls it a bold move, especially since we often want to protect ourselves. She often tells this story when coaching other people.
  • Amy knew at the time this program was not good for the business and wanted to ensure her name was synonymous with understanding what was good and what was not good for the business. *“That’s what a business review should be – whether it’s working, whether it’s…. It showed that I knew what was true and I was unafraid to say what needed to be said.” – Amy Lewis
  • Amy likes to emphasize the right kind of metrics and prevent others from focusing on vanity metrics.
    • “Telling those stories and telling people what to demand out of their metrics is part of my personal brand. People know if I show up with metrics, I’m going to know them. They are going to be true, and I’m going to tell you what it means and not just what’s on the paper.” – Amy Lewis
• Nick calls this the other side of the coin. If we’re going to tell someone what they are good at, why not be honest and tell them what they aren’t good at with an assessment of the situation?
  • Looking back, being honest in that business review and telling the truth when it was very uncomfortable was a form of storytelling.
  • Amy had the business acumen, was curious, could do the work, and proved she could lead a program. This put her back on the path to product marketing.
  • John says this is building a personal brand of telling others when someone is not working.
  • Amy mentions she is a headline person and has made a career on some catchy phrases that stuck. We can speak truth in a way that softens the blow but also in a way that makes it harder for people to ignore.
  • This is marketing at a feedback mechanism. Would you rather be around people who will tell you there’s a problem while you are in the room or talk about it when you are not in the room?
• Amy has mentees that often ask her how to work with executives.
  • She gained access to executives from being on social media in the early days when the playing field was more level. Consistently showing up on social media allows us to engage with anyone.
  • Amy has interviewed a number of executives over the course of her career based on the nature of her role (i.e. she had a lot of access to them).
  • These two things made it very normal for Amy to engage with executives.
  • The person who hired Amy full-time at Cisco gave her a business book that discussed the concept of executive inoculation.
    • One simple example of this is when a president doesn’t know the cost of a gallon of milk because they have lost touch with the people.
    • If a business leader has nothing but “yes” people around them, it can lead to executive inoculation.
    • “When you become disconnected…from your persona, from your audience, your business…that’s a danger. There are always going to be executives that wish to stay inside that bubble….” – Amy Lewis
    • The majority of executives Amy has worked with appreciated honesty. We should be thoughtful in our choice of language, stay true, and “bring the receipts” (or the proof) as Amy says.
    • “You can say hard things if you say them nicely, if you’ve built trust, and if you bring the receipts with you.” – Amy Lewis

48:42 – Becoming the Interviewer

• Was the interviewing something Amy had done previously and something she needed to apply to an executive audience, or did she have to learn interviewing on the job?
  • Amy is thankful for mentors like the person who hired her at Cisco as well as Brian Gracely of TheCloudCast.
  • “Though the story sounds good now, what I didn’t know could fill an ocean.” – Amy Lewis
  • Amy worked a few cubes down from Brian, and he was willing to help her learn many things.
  • Amy came up with the idea of Engineers Unplugged, and it was almost like a gameshow / competition with 2 engineers and a whiteboard.
    • “Once more I come up with a headline, and I write the story around it…. I had zero percent experience on camera before Brian Gracely challenged me to get started. And then I just took natural curiosity / extreme nosiness and put it to work. I thought if I’ve got the microphone, how can I serve the audience? How can I ask the questions that everybody wants to know?” – Amy Lewis
    • Through this exercise, Amy had to get comfortable with being on camera.
  • To this point Amy had not interviewed people but had plenty of practice public speaking. She did debate in high school and college and has given speeches to small audiences and those up to 3000 people.
    • “In some ways it almost felt like interviewing easier because I’m trying to make them successful…. And I’m always a winger on the soccer field…. I’m there holding the microphone to make them look good and feel comfortable.” – Amy Lewis

Mentioned in the Outro

• Being a winger in our careers doesn’t sound so different than being a mentor. Amy talked about seeking mentorship during different times in her career and now mentors others. If you’ve never worked with a mentor and don’t know what to expect or how that relationship should work, go back and listen to these episodes with Dale McKay:
  • Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2)
  • Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2)
  • May you be blessed with at least one great mentor in your life!
• Amy has recently launched the Unicorns in the Breakroom podcast with Sarah Vela. You can find a discussion with thoughts on return to office mandates in episode 1 of the show.
  • Unicorns in the Breakroom on Apple Podcasts
  • Unicorns in the Breakroom on Spotify

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [e-mail]
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  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.