Year Two

I remember the precise moment in 2018 when it happened—the very second an ephemeral moment of clarity so farfetched as to seem entirely fabricated and yet so starkly vivid as to be indisputable.

I was sitting in a boardroom meeting with two coworkers and two senior representatives from a potential partner. I won’t name names.

There was a pair of awkward, white floor vases filled with plant-like-but-definitively-not-plants “sticks” which framed either side of a dormant Xbox One tethered to a sizable Toshiba, which itself had a penchant for making the resolution of any connected computer so damn high that each meeting invariably started with ten minutes of “go to your Settings” followed by “I know, these 4k TVs, I tell ya. I saw a good deal at Costco…” and ultimately a “People on the bridge, still on the line?”.

The room’s centerpiece was a wooden table which bore the kinds of stains that at first blush suggest it had seen some serious boardroom brawls over the years but was in fact merely representative of the fact that no one saw fit to clean up after themselves when spilling coffee in a meeting. Thankfully, the lingering faded black trails of marker which couldn’t be erased from the whiteboards that adorned the walls around complemented the table’s dark veneer.

The goal of this poorly-organized meeting (as I came to understand it mere moments before it began) was to determine how exactly this potential partner would help us execute on a specific product opportunity we were exploring.

Prior to this meeting, in the absence of any concrete information about the use case, I had done weeks’ worth of research: customer discovery, value proposition design, pain quantification, use case definition, total address market valuation, competitive analysis, minimum viable product validation, roadmapping—more work than anyone else involved by at least dozens of hours.

By this point, I was advocating for the shelving of this particular enterprise. The economics had way too many flimsy assumptions; the TAM was suspect; we’d not yet found meaningful validation; and we were nowhere near clear on the what, why, and who to bring a partner into the mix.

Suffice to say, I wasn’t into it, and those that know me will tell you that a Frank disengaged is a Frank disembarking.

You may then be able to imagine both my face and my mindset when, as the meeting started, our first discussion point was not of the customer nor the pain nor the use case nor even the economics but rather the technology—the how to a what and for a who that we didn’t understand nor could articulate as a group uniformly let alone individually and (or) intelligently.

That the meeting diverted a moment later towards discussion of a side letter to sell crypto in a quantity large enough to warrant both a private plane and the giant duffel bag of cash which was then set down on the boardroom table only served to punctuate the end of the sentence for both my product career and the journey started in Year One.

My time in product management and in tech start-ups had run its course. I accepted an offer from Salesforce the following day.

So ended the first leg of my career. That was 2018 in a nutshell for me: a bag of cash on the table before me, the cost of which was walking myself into the wrong room.

Year On[e] Where [e] = “ce More, With Feeling”

We all begin the year with the best of intentions. Only the best of us can see those intentions through briefly before falling back into the status quo after forgetting the what and the why amidst the here and the now.

We are only human, after all, and habits are hard to break; Instagram ain’t going to scroll itself; swiping right feels good; the gaming backlog is forever growing, etcetera. At least, that’s what I tell myself to assuage the pain, particularly in the wake of last year.

For you see, Year One was full of aspiration, full of positivity and of optimism and of endless opportunity.

Year One was resolved to be the comeback story, the redemption tale, the coming of age saga that would so triumphantly (and, *gulp*, publicly) follow a year of divorce and career disruption and financial discombobulation.

I barely made it to Q2‘18 before that resolution fell apart.

Look, I could easily spin the story the other way. I could join the ranks of self promoters on LinkedIn and Medium who are trotting out platitudes and “you can do it sluggers” while humble bragging about how I have it all figured out and you can too by following this listicle and subscribing to my newsletter so you can get your fat stacks and Lambos and your exclusive invite-only beta key to www.blooddiamond.com.

But that’d be all bullshit brand building. It’d be selective truth, if truth at all. It would be me playing to the LinkedIn “listicle leaders” and masturbatory Medium “magnates”.

Rather, I want to focus on what’s more important: what didn’t work, why, and how I iterated through it. After all, real iteration comes from constant awareness, dedicated introspection, vulnerable humility, and continuous improvement.

So let’s talk about how I ended up in that wrong room and what I did about it, because that’s my story of 2018.

What Went Wrong

Freelancing

As was the central thesis for Year One, I saw 2018 as the year I would finally embark on doing what I wanted to do: tell great, impactful, and catalytic stories professionally.

However, I made the mistake of assuming that realizing said vision would require going it alone as a freelance writer. It took me months thereafter to realize that (for me) freelancing funking sucks.

Doing biz dev and lead gen for effectively a “content” company simply isn’t my cup of tea, and that amounts to 90% of what you do as a freelancer, which was a surprise to virtually no one but I, apparently.

Should I have heeded the advice of the many attempted-freelancers who’ve written at length about that reality? Probably, but them’s the breaks for an experiential learner. Unfortunately, that learning came at a heavy cost both personal and professional.

In short, I decided to spin down and close the side business entirely. I know that storytelling must be central to my day-to-day working life, but I’ve now empirically validated that freelance writing just isn’t for me.

Failing Forward

The failure in freelancing sent me tumbling into the abyss when trying to chart the right next steps for my career. I floundered, bouncing indecisively from company to company before ultimately settling more from fear than excitement.

This act, unsurprisingly, had a number of consequences, some obvious and some less so.

Above all, I faced a significant amount of scrutiny from peers and potential employers, particularly those I was pursuing for non-product roles. Choruses of “you don’t know what you want” and “you’re a flight risk” echo in the faint memories of the last 12 months’ experimentation.

Yet, in the wake of that difficult period, I’m left feeling angry at myself—not for the job jumping but rather for not being able to better articulate the way I feel about job jumping when pushed on it.

Every career move I’ve made has been for a specific reason, and I take great umbrage with the double-talk in the tech industry around iteration.

I run my career as I have the most successful products I’ve managed. I iterate. I learn. I adapt. I ship. Shit breaks. I learn. I adapt. I ship again. Shit gets better. Money is made. Customers get upset. Something new and shiny comes along. I ship. Shit breaks. I learn. I adapt. I ship again.

I don’t sit idly by incrementally improving myself by tackling small tweaks. I don’t ride rocket ships to take credit as a conveniently-timed passenger. I don’t uphold the status quo, and I don’t stick with it because optics or because bonuses or fucking just because.

I tackle each job with fervent dedication to making an impact (1), making customers happy (2), and making myself better (3) for the next big challenge (4). When one of those four critical must-haves are no longer (or never really were) on offer, I waste no time making the move that’s in the best interest of my career.

Great businesses don’t waste time selling to customers who don’t want their product or don’t want it to improve, and I run my career with that same mentality. Sometimes that hurts companies; sometimes that bothers recruiters; sometimes that ruffles C-level feathers. I have no qualms with that, and I’m not ashamed of it.

But not every company wants to hear that. Not every company is up for that. And that’s okay—but it took me way too much of 2018 to realize I need not apologize for that belief and, really, my values.

How I Iterated

Partnering Up

Thankfully, I was able to find a company of folks, really partners, who were and are supportive of said mentality and who helped turn the year around and set us all up for mutual success in the year(s) ahead.

Had I not sought out the help from those around me, and had they not answered the call, I can only fathom how much worse things could have gone. They are eternally deserving of recognition and appreciation therein.

My parents retired this year, and my in-laws made a big move to downsize their long-standing adobe, so I would be remiss for not calling out my family first and foremost. Kev, Sam, Al, Ma and Pa Caron, Ma and Pa Vite, and my brother Joseph all played a crucial role in being a steady constant amidst the sea of change.

In my personal career, I was supported by some key folks during my freelance journey, including the City’s treasure Paula Kwan, the entreprenurial Anthony Zanfini and Yasser Pervaiz, the effervescent Katie Paterson, the indomitable pair of Kim Phelan and Amanda Pardy, and of course the legendary Tiffany DaSilva of Flowjo fame—all of whom provided both leads and moral(e) support during my freelancing stint.

I was also lucky to work with great folks like Jill San Luis, Matt Barnes, Max Van Lyl, Jeff Kraemer, Kiley Meehan, Jeremy Bailey, Lindsay Rothman, Jane Flanagan, and Scott Williams while at FreshBooks. Each played a role in my rationalization of product management, marketing, and the art of corporate storytelling—which is particularly telling given I worked with each for all of a hot minute.

Yet, I was luckier still to lead a team for a spell with great folks like Chris Gurney, Nick Pinto, Mike Laccetti, and Bhavin Shah while kickstarting the Product team at Globalive Technology. I take pride that I was able help set each up for success in their own respective path while focusing our efforts there in the end, and I’m grateful to each one of them for helping to facilitate the next step in my own career.

But most of all, I was supported immensely by Vanessa Vite, Paul Snelson, Amber Morace-Wohng, Ian Wong, Matt Roher, Adil Jaffer, Pablo Romero, Jeff Blanchard, and my trail guide Ming Fong as well as a huge, extended Ohana at Salesforce.

Which is another great segue. Man, I’m killing it late in the game here.

Braving The Unknown

The most significant “right” of the year was, after much experimentation and self reflection, making the jump out of Product once and for all to join one of the world’s leading business-to-business (B2B) software companies.

Salesforce is a company I have admired for years, and as I’m learning more about the platform and what it’s capable of, I’m increasingly hyped to work with some of the amazing businesses in Canada during the year ahead. I’ll have much more to say on this in the coming months.

What’s important to highlight here for now, though, with respect to what went right is the rationale. Scrutiny over my job jumping in the last 12 months notwithstanding, I’ve been pinged endlessly to try to explain what seems impossible to understand.

Why leave product management, and why pre-sales?

I’ve written before about my rationale for leaving Product Management (PM), and I’d previously believed that Product Marketing Management (PMM) was the only sensible way forward for me. However, in walking that path, what I’ve found is that PMM is itself generally fraught with similar realities and similar foci to PM (along with marketing-focused activities like demand gen which aren’t my speciality).

Understanding the move to pre-sales, then, requires understanding what excites me about my work, both in PM and PMM and in general.

I love stories. I love developing a deep understanding of an audience. I love doing the creative work to figure out what moves them and what’s important to them. I love drafting and writing and producing a story that engages their senses to excite them towards action. And I love the performance art that follows in delivering that story.

That was what I loved about PM and PMM: the tech and working with dev was always just a necessary (though at times enjoyable, to be sure) means to an end.

What mattered, and what’s hard in tech companies, is telling a story which connects meaning and value and purpose to product—to every unique customer in unique messaging and positioning every single day. That’s the day-to-day province of sales engineers and sales people, not so much PMs and PMMs—at least not based on my experience.

Product Management, at its core, is chiefly about risk mitigation. It is about prioritizing the next best action to ensure the org continues to grow its customer-base and customer value strategically. The day-to-day involves understanding, making, and facilitating strategic product trade-offs.

Product Marketing, at its core, is chiefly about demand generation. It is about understanding who the buyer is, where the buyer is going, and why the buyer cares in order to define the strategy that will arm both internal and external stakeholders with a story that drives a buying action. The day-to-day involves understanding, making, and facilitating strategic marketing investments.

Importantly, Product Management does not have the monopoly on deep customer empathy, and Product Marketing does not have the monopoly on customer-centric messaging.

These roles involve storytelling, to be sure, but said art isn’t their daily focus. On the contrary, Sales Engineering is corporate storytelling incarnate. Sales Engineers spend each and every day doing nothing but deeply understanding an individual audience and delivering a story to them that connects all the dots.

Sales Engineers are enabled by PMs and PMMs with tech and talk tracks, sure, but only Sales Engineers (and the Account Executives they partner with) spend virtually every day becoming better and better storytellers and writers and performers—artists.

And while it may sound radically more tactical a role, it typifies exactly the niche I’ve been trying find for ages—the natural progression from tech writer (written wordsmith) to product manager (plot structurer) and finally product marketeer (curated rhetorician).

Now I need only prove myself up to the task.

Retrospecticus

I’m left coming back to the story of the crypto bag of cash and the significant cost of being in the wrong room.

I wish I had allowed myself last year to put myself in the right room the first go around. Alas, hindsight is BTC$20.20 and I suppose that would have made the year boring af (2018™).

Given my recent history, I won’t hazard any major promises or predictions for the year ahead. I also won’t touch on all the personal changes ahead, from finally ditching Facebook products to my intent to break my annual tech device upgrade cycle this year and beyond. That’s for another day.

Instead, what I will wrap this blubbering up with is this. I look back on the year past proud of my growth as an individual and as an individual contributor, and I look ahead excited to make an impact at Salesforce and for the businesses that I will work tirelessly to help in my new role.

2018 was a year of tremendous experimentation and self-education, and I couldn’t be more excited to move forward in 2019 with an ever-increasing appetite to learn, iterate, grow, and help.

Here’s to finally making it to the right room. Now I just need to figure out how to stay in it.