AMA: F20 Strategy Director at 25 Y/O

Dedline's picture
Rank: Neanderthal | 2,593

Overly caffeinated and procrastinating on some technical writing that needs finishing.

My path:

  • Top 25 Undergrad with concentrations in Management Information Systems and Supply Chain Management with a 3.2 GPA but strong work experience
  • Four years of grinding through a blue chip technology company in a technical sales development type of program
  • Accepted an offer at a F20 company as a Director of Strategy in an industry vertical focusing on GTM strategy, executive presentations and strategic partnerships

I credit the successes that I've had thus far to a compulsive obsession for the game of "career" and a lot of luck along the way.

Ask me anything!

Comments (40)

Feb 2, 2019

What ended up drawing you toward sales? Also curious as to where you want to end up.

Feb 3, 2019

Hey Billy,

I actually tried to land Tier-2 IT Consulting gigs (e.g. Deloitte BTA, Accenture IT) but struck out because I sucked at the case method and my interviewing demeanor was rough. Months prior, I had spammed my resume to any job posting in big technology that had an inkling of IT Strategy. I had already accepted a Tier-3 Healthcare IT Consulting gig when the blue chip technology company (arguably Tier-1) called asking if I wanted to interview for their technical sales development program. So although I never considered "sales", what I didn't know is that there's so many different flares of sales and this was the absolute most technical / strategic you could be on the sales and distribution side of thing. It was a perfect fit.

Not really sure where I want to end up. I'm in the process of trying to get an MBA sponsored, but I'm also thinking about just cashing out my RSU's in 2 years and heading to China to work on their healthcare system... I'm a believer that hard work creates options and big decisions make themselves.

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Feb 2, 2019

Curious what it was like in sales and how that experience got you to strategy.

"Truth is like poetry. And most people fucking hate poetry."

Feb 3, 2019

Hey @aphenophilia ,

So the job at my prior employer looks a lot like this posting. To generalize, I had to know the healthcare technology stack / landscape cold, create proof of concept / prototypes pertaining to the hottest technology trends and sell the living daylights out of that solution (e.g. NoSQL Databases for unstructured doctor's notes, Cloud Compoute resources for sequencing genomes) to a client or at conferences.

By year three on the job, I had SME-level knowledge about healthcare industry and I had all pertinent technology reference architectures (example) burned into my head. I would never consider myself a developer, but I could hack together a working prototype with a bit of help in a few weeks. And probably what makes me the most valuable, I could distill down ideas and communicate them effectively to an audience who wasn't as deep in the weeds.

My job now is very much the same thing. Study the product portfolio, orchestrate product mixes to create solutions that the healthcare industry needs and craft the pitch / sales collateral that our seller's take to market.

About technical sales life -- You'll hit Gold Status on AA, you'll get $70+ a day to blow on meals and you'll go to cool events with clients and vendors. I'm a bit jaded now and couldn't give two shits about vendors buying dinners / drinks / events because you have to sit through hours of them explaining a solution for hours that could be understood in 2 minutes if they provided a system context diagram + a technical individual to answer specific questions. The clients for the most part are nerdy, middle-aged men who managed to slog their way to a senior leadership position and they treat you like a lesser because you're trying to sell them shit. Add to that, I'm young and have more in common with their 21 year old son than I do with them.

What I try to do now is stay back, develop solutions that actually move the needle, speak at conferences and only take client calls if I think it's going to put my name up in lights for senior leadership.

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Feb 4, 2019

Summit?

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Feb 2, 2019

What's your salary?

Feb 3, 2019

I'm struggling a bit with this one. I just never see directors this young.

I know one who did this at similar age but he jumped from PE fund to a director role at a portco.

What's your total compensation? (Salary/bonus/stock) Feel free to adjust the numbers slightly for anonymity.

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Feb 3, 2019

Hey @SAAS CFO & @Sunshine Funshine ;

I am very young for the position. The second youngest director on our floor is late 30's. True story: I was actually bullied the first couple weeks on the job by a group of younger guys (30+) who I would have otherwise naturally gravitated to for friendship. They drink, golf and go to dinner with the wives all the time and I've never gotten the invite. But I've earned my spot and I don't get paid to fit in or make friends at work.

Comp (round numbers for ambiguity):

  • Salary = 150K
  • Bonus = 60K
  • Stock = 50K
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Feb 2, 2019

How does that negativity of your co-workers impact your work?

Feb 3, 2019

I mean that's D comp for sure. (more than I make haha) I'm still surprised, but good for you.

I'm sure you are a rockstar, it's just that most of the time even junior rockstars don't get Director positions due to the fact that Directors are generally expected to be able to lead and train staff, and advise senior leaders.

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Feb 4, 2019

walk us through the interview process...specifically any concerns management had w/ your relatively limited experience and how you mitigated or spun them positively

Feb 3, 2019

Hey @td12 ,

For all the positions that I applied for, I usually had 90%+ of the technical skills / domain knowledge / experience that they were looking for so that wasn't the issue. The issue was always years of work experience. After being rejected so many times by headhunters / recruiters that would ding me on this fact alone, I got pissed.

I had been competing and winning against peers 20+ years my senior for two straight years. I knew the new technologies, reference architectures and use cases equal to or better than my peers. I always won on public speaking, content and personality. And to top it all off, I was starving.

The people that you're competing with for these positions are not impressive by WSO standards. They're middle-aged, institutionalized and for the most part, they're content waiting for their turn. And honestly that's totally fine, but that's not who I am. What turned the tide for me in these interviews was confidently affirming there was no doubt from a skill / experience point of view and tactfully voicing that I wasn't scared of competing with candidates with 20+ years in the business; on the contrary, I couldn't wait to take their spot.

When I would go in for interviews, I was very conscientious of coming across as older than I was. You're an actor in this process and you have to play the part. I would wear perfect, of-quality black shoes, black slacks, black belt and white dress shirt to convey "conservative, white-collar". I would rock an un-groomed 5 o'clock shadow that I am able to get away with because everything else on me is dialed in (hair, eyebrows, etc...). A trick I learned early on is that the sage / smartest guys in the business would rock the most boring fucking sports coat you can imagine. Noticeably boring. Like shit off the rack at Sears. As a quick aside, the more sage you became in the tech industry, you could pull even crazier shit like wearing a pony tail or watching Twitch Streams at client dinners. Back to it though, boring ass sports coat and I always brought my black padfolio and took paper notes during an interview to again, "date myself". Obviously, deflect any veiled questions that could possibly give away your age.

I can go way deeper than this hahaha ;)

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Feb 4, 2019

You mentioned an obsession with the game of career- Can you elaborate on this a bit more? Some of the general things you do/did to better yourself, the things that you think would help anyone in their career. I'm always trying think of what more I could be doing- what books to read, how to work on executive presence, what random skills might be helpful. So be as specific as you want! any and all detail is great.

Thanks!

Feb 3, 2019

Hey @dan_yo23 ,

First, develop a keen sense of self-awareness. Understand how you're perceived in social situations. If you're rough in social situations, read "How to Win Friend and Influence People" 5x and just let it sit at the back of your subconscious. Tweak your personality to be an "interesting character" in a social situation.

Work on your insecurities. When they come through in dialog and body language, they're unpleasant to others. Learn to love yourself.

Your appearance matters. Go to the gym, eat healthy and maximize god-given aesthetics; you have no excuse not to. People do not have respect for people who do not respect themselves.

I think EQ / Self-awarness is sorely neglected in business and is a massive competitive differentiator as you move up. Spend a significant amount of time here.

Really not much more to "Game of Career" other than I'm very passionate about career. There's a lot of people who view it as means to an end. That's not me. A comment on this forum by @brotherbear was eerily close to describing the "obsessive compulsion" I feel.

I asked WSO that exact question regarding Executive Presence

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Feb 4, 2019

Great stuff. What are some ways you work on EQ and self-awareness? I'm interested in the gritty details- I've been reading multiple books on and around the topic, and have been actively putting what I've learned into action. That said, I'd love more detail more targeted towards someone actively working on the topic. Thanks!

Also, you mentioned in another response that during your interview you made sure to dress and act in a way that made you look older/more experienced. Did you leave dates off of your resume and linkedin? how did you keep it from being obvious that you were only 25 and 4 years into your career?

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Most Helpful
Feb 3, 2019

Hey @dan_yo23,

EQ: I've spent the last 10 minutes sitting at my desk thinking about how one works on EQ. I think it boils down to having a genuine curiosity in wanting to understand a person and studying interpersonal relationships. Instead of going through life as is, watch and listen to how people interact. I've read a lot of books on body language (the best one was an FBI course I found on the DarkNet), picking up women (Art of Seduction, The Game, Vin DiCarlo's stuff) and a ton of self-help / leadership. I don't take any of it as gospel, but it's all context / variables as to how things work and why people do what they do. You continue to build upon this corpus by experiencing a variety of social situations. The more uncomfortable, the more you'll learn. As you continue to compile these profiles / stereotypes of people and interactions, you'll be quicker to recognize the patterns in real-time and you'll be able to give them what they want / need. Two final comments: 1.) Ask questions and listen to learn. Test your hypothesis as to why something is by asking another question or throwing out a statement to see the reaction. 2.) Hang out with women. Women are 1000x better than this shit than men are. Be friend them and learn from them how the world works from their lens.

Self-awareness: I think self-awareness and EQ go hand-in-hand. I don't advocate this, but I took an 1/8th of psilocybin mushrooms during my sophomore year of college that changed my life. Without sounding too much like Joe Rogan, it unlocked my subconscious mind that I know have access to? This could be just general anxiety, but I now have this real-time compute engine where I think through a lot more of what I say, interpersonal interactions, power dynamics and what hand I want to play in an unfamiliar situation instead of going off of gut instinct. I can go on runs where I know I've nailed the optimal interaction without thinking, but it's not often (It's getting better though). It's been a blessing for unfamiliar social situations but I have a really hard time shutting it off. In my time away from work, I prefer to hang out with long-time friends where I don't have to analyze because nobody is jostling for favor / power in our long established friend group. I try to stay away from people who are insecure, obnoxious or dominate the conversation -- it's exhausting. @APAE came up with an awesome little framework under "1. Know your Audience" to generalize self-awareness that's definitely worth the read

Resume / LinkedIn: Nothing would give away my age. Graduation dates on undergrad have been redacted. I've cut out all my internship experiences (3 years in total) because although I did stay on year round, they are lowly enough to infer that I was indeed in college at the time. At this point in my career, the experiences would detract from the profile that I'm trying to convey. Those years of experience have been relegated to the verbal tally's on the years I've been in the industry and war stories from, "... when I worked in the trenches". I've disabled the "...You might also know" feature on the right-side of my LinkedIn because my buddies from college were still showing up when people would hit my page. All of my copy reads very technical and scientific with very little hyperbole. I've disabled skills and recommendations because I believe they are also detractors. Clean, simple and professional.

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Feb 4, 2019

I also am surprised by your age and position, especially in a fortune 20 company, especially as an external hire. Good for you.

Do you manage people directly under you or are you an individual contributor?

Are you in the same industry your technical sales role was? How has the transition been from deep in the field to insulated in the organization?

How are you gaining credibility with senior leaders with such a gap in age and experience?

Feb 3, 2019

Hey @2trickpony ,

Individual contributor. I'll have to manage a team to get to the next level. Not sure how I feel about that yet.

I am in the same industry (healthcare) and I don't think I'll ever leave. It's too large of a competitive differentiator, I find it fascinating and although further removed, there's a level of altruism when my solutions help to improve clinical outcomes and quality of life.

The transition was brutal. Technology -> Business is not easy. The politics are way more in your face and you have to learn how to pull corporate levers. The stakeholders are very different. My clients are no longer technical; they're business people who deal in technology. Perfecting a compelling abstraction for this audience took months to dial-in. But now that I "get it", I think it's a better fit for who I am than my last job.

What I miss the most is working with people who were virtuoso in their craft (e.g. Computer Science theory, Java programming). The people who knew how deep the well was. The people who would off the cuff string together several theories into a cohesive, communicable thought. The people who could programmatically / systematically implement highly-complex idea in a matter of days. Sometimes, I feel like a sleazy knockoff of these individuals and that business is a bunch of jack of all trades but masters of none. But most of these highly-technical individuals would never succeed in a business capacity. I personally believe the technical route is more noble, but their career ceilings are much lower than a person working on the business side of things. I'll always be humble in my career for meeting / understanding these types of individuals.

Regarding credibility with senior leaders -- I've got an updated LinkedIn that's stacked with projects, certifications, patents and coming up on what is a cumulative decade of industry experience. I carry myself as a consummate professional whenever I'm on the clock / taking calls. I know I know more about the solutions that I've helped to orchestrate than they do. Credibility is a non-issue.

Something that would be interesting is developing a personal relationship with Senior MALE Leaders -- I don't even bother. These individuals are usually my father's age and older. I'm not married, I don't own a house, I don't have a dog and I don't listen to the fucking Rolling Stones or Bruce Springsteen. I've got a girlfriend, I live in a high-rise apartment, I'm afraid of being responsible for a dependent, I don't think about having kids and I'm still slamming shots of whiskey back with my boys before hitting a basketball game or a Young Thug concert. Sure, I'm missing out on the good ole boys network that @DickFuld touts, but that's really not an option at my age.

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Feb 4, 2019
Dedline:

I'm missing out on the good ole boys network that @DickFuld touts, but that's really not an option at my age.

What network have I referenced previously? I most likely referenced people who know my work and would hire me in a nanosecond because they know what I can produce. I don't know anything about a good ole' boys network. That wouldn't be me.

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Feb 4, 2019

This response somewhat confuses me. I get the politics you reference (working at 1 of 2 companies in F20 in Healthcare solutions, they are super political messes), but you saying that contradicts that an updated LinkedIn profile stands for itself. At a Director level, you are constantly engaging with senior executives, especially in a strategy group. They don't have time to read through an online resume, they go off of gut, which is built with time and experience with your work...deeper than being a consummate professional.

Also, isn't the trick to being savvy in the corporate jungle developing relationships with those senior leaders who aren't your type on surface?

Not afraid of the MS, but I feel either your youth is coming through slightly in how you view your position (in which I say get a GREAT network of mentors to navigate your sudden proximity to the sun), or you are over-inflating your role (in which I say, why?)

Feb 4, 2019

Anyone getting Brady vibes here? I sure am.

Feb 5, 2019
Dedline:

I'm not married, I don't own a house, I don't have a dog and I don't listen to the fucking Rolling Stones or Bruce Springsteen. I've got a girlfriend, I live in a high-rise apartment, I'm afraid of being responsible for a dependent, I don't think about having kids and I'm still slamming shots of whiskey back with my boys before hitting a basketball game or a Young Thug concert.

Sound like my kinda guy

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Mar 7, 2019

But is it even the American Gardens building on West 81st street?

Mar 7, 2019

Technology is absolutely exploding right now. Everything is getting upended. Unlike finance, actually domain knowledge/experience is rare.

Feb 4, 2019

Congrats on getting where you are at such young age. I'm sure you work hard to get there.

I'm curious about your hiring manager. S/he obviously sees something in you to take a chance. Can you share his/her background? Thanks.

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Feb 3, 2019

Hey @aphoegyi1989 ;

Looking at your posts, it looks like you're also a younger director. Prost m8!

Very interesting question but I'm going to take a pass on this question as I wouldn't be able to disclose the level of detail I believe you're looking for.

Hope you understand brother.

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Feb 4, 2019

Completely understood.

I made FP&A director at 28 (about to turn 30 now). It's very rare at my company but I started out as an intern so 1) I was not the new guy and 2) I had good references from executives who knew what I can do.

With that said, it's very difficult to break into director/VP level as a young external candidate unless there's a manager who values the capability more than length of experience. That's why I asked about your boss.

Feb 25, 2019

This post was inspirational. Between the main post and your responses I have changed my perspective on my trajectory as well as my linkedIn profile (great advice here). I hope you continue to kill it in your role and get recognized for it!

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Feb 3, 2019

Thanks bro and best of luck clawing your way through the ranks ;)

Mar 7, 2019

Thanks for doing this, very insightful so far. In terms of "career," people/employers like to see well-rounded candidates that are passionate about things outside of the workplace (charities, involved in industry groups, etc.). Other than what you've already mentioned, is this something that you've done and/or encourage doing? I'm sure it helps candidates' applications look significantly better.

Feb 3, 2019

Let's set aside acts of benevolance / passion and focus only on "career". I believe that just like all career decisions, choosing to donate your time to a 501c3 or participating in a professional organization should be weighed via opportunity cost / benefit x the profile you are crafting.

I currently do not donate my time to a 501c3 for the purpose of advancing my career. I did do this in college in order to get experiences that I wanted but could not attain at my age + CV (e.g. small business consulting, teaching 20 students the fundamentals of programming at a university level). Last year, I tried to jump on the board of a large local non-profit but was not selected. Most boards will straight up ask you for 5K for a seat at the table with a commitment to help on "fundraising" efforts. So 5K + 5 - 10 hrs/week (at a junior level) asking people for money to get on a board. Maybe it's just not my personality type, but the whole thing just didn't sound like a good time.

Would love if someone could teach me how the non-profit board circuit works.

Professional organizations is a mixed bag. In healthcare, HIMSS and CHIME are the big ones. Essentially, if your corporation is in the healthcare tech space, they probably already have memberships with these organizations. They host the largest conferences, they offer professional credentials that you must qualify / test into and most importantly, they are organizations comprised of the who's who of healthcare IT. For me, I don't need my professional experiences qualified via professional credentialing but there is an interesting one from CHIME called CHCIO (basically validates you could perform the duties of a CIO for a healthcare provider) that would be interesting if I wanted to make the switch from vendor to provider. I try to stay close to the conference event coordinators because they control who speaks at the sessions; this is by far the largest value for me. This is how I get my name, my ideas and really, the only way I am able to meaningfully network with individuals higher up the food chain. The PR coverage and how it reverberates across the internet and our corporate social media echo chamber makes me an extremely visible individual compared to my peers.

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Mar 7, 2019

Nice work!

-Is it a technology company? If that's too specific - What stage of maturity are they in their "IT Transformation"? How progressive are they with legacy systems, processes?

-What is the culture?

-Are you on the West Coast? Your company leadership/clients/partners? Any interest/pressure?

-What other options did you consider? Sales Rep? Startup? I know you said MBA is still on the table.

-Are you still entertaining potential clients/partners? Are the dinners less common/boring?

-Are your new coworkers/clients impressive/competent? Interesting?

Feb 3, 2019

redacted

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Mar 12, 2019

An individual contributor with a director title? Talk about title inflation.

That level of comp for a strategy role where you're not managing people is a bit odd. The job seems somewhat specialized and technical, though.