100 Days as Tackle's Chief Cloud Officer

For us road warriors, the last 12 months brought a lot of change. Gone are the days of maximizing every minute on a call before the door to the plane closed for take-off. GoGo wireless went ByeBye for a while. Our mobile phone use evolved yet again. Remember when we held those things up to our heads, think back to when you wore dress slacks. Then the wonder and brilliance of AirPods leaving the phone in the pocket of your jeans. And now, video conferencing in full HD while in your workout shorts and a polo shirt. 

I haven’t lived this drastic of a change in work behavior since I packed up and moved to Australia in 2012. While a serious business climate, Aussies seem to have found work-life harmony. My days were filled meeting with customers and partners and the team, but nights and weekends were about family and friends. The concept of keeping up with the Jones’ wasn’t allowed to exist. For the most part, stores closed at 5pm, except for late-night shopping Thursdays (that’s a real thing). I promised myself to take these new and improved living habits back to the US. As you might guess, as the time passes, those habits get replaced by new ones, or maybe in this case the old ones surfacing again. Historical performance can teach you a lot about the future, and the pandemic has given us all another chance to decide how we want to work going forward.


Season of Change

While the initial months of the pandemic had folks hunkering down in their jobs and thankful for ongoing employment, the surging economy that followed brought confidence and new opportunity. One of my last business trips of 2020 was to the Amazon Web Services sales kickoff in Chicago where I met Tackle.io co-founder Brian Denker. We share a passion for changing the world of B2B commerce and the emergence of software Marketplaces from the likes of AWS, Microsoft, Google, and others. Not long after that initial meeting, I joined the Tackle advisory board and enjoyed interacting with some great Marketplace minds changing how their companies look at go-to-market. Late in the year, I found myself considering a departure after 10 years with an amazing company to join what was then a Series A startup. Feb 15, 2021 was my first day as a Tackler.

Read my blog post on shaping the future of cloud as Tackle’s Chief Cloud Officer.


Reflecting on the First 100 Days

You would think going from a 7,000 person global organization to a 50-something person (now approaching 100 just 3 months after joining) remote-work early-stage company sends a bit of a shock to the system. No doubt it does, but it’s a positive shockwave that gets the RPMs of your heart and your mind back to peak performance. After a fast-paced start, it’s great to look back at my first hundred days at Tackle. There are 5 things that stand out and make me incredibly proud to be a part of this company.



Recently our senior leadership team (all fully vaccinated) gathered for an offsite. As a few of us joined during the pandemic, this was our first time meeting in person. We had a well-balanced agenda of business topics and time to (re)connect. I was ready to meet my colleagues at baggage claim. I’d spent the weekend engrossed in the ReadMe docs of each of our exec team members….like a guide to working with a colleague. What an amazing way to get to know someone. Work habits, hot buttons, family, expectations, quirks, communication preferences…all in well-written documents or slides. (If you want some great examples, check out these ReadMe masterpieces from which we pulled inspiration for our own) It was amazing to learn how each of our leaders thought about their roles and common threads emerged: customer-obsessed, unselfish, transparent, goal-oriented, inclusive, value creators, masters of their craft, lifelong learners. When a leadership team is aligned both on strategy and on culture, beautiful things happen. I went wheels up to go home later that week knowing I joined an amazing team.


Riding on the Shoulders of Giants

From my earliest days in alliances and business development, I have always operated with a swing big or go home attitude. Done well, strategic partnerships fuel non-incremental gains by driving innovation, opening up new routes to market, and building brand recognition by standing on the shoulders of giants. For 99% of the companies on the planet, to partner with the cloud leaders, you need to punch above your weight class. This takes strategy, energy, strength, and most importantly belief. To earn the attention of these alliances, you have to believe you can deliver real and lasting value to your partner and to their ecosystem of partners and customers. I spent enough time with Tackle in 2020 as an advisor to know the company had something special. As I sit in the seat day-to-day my confidence grows as our partnership efforts are driving fantastic customer outcomes, our partner-generated lead flow increases, and the initiatives we are co-investing in are market changers. 


Embrace (or Dismiss) Feedback

Think back to the last time you were in a company that truly encouraged and embraced feedback at an executive level. Now think about what you were allowed to give feedback on. Tackle is a place that welcomes feedback on how executives are doing their jobs. As in, how am I doing for the business, how am I doing for you and the team, how could I be better at it? It’s vulnerable for sure but it’s also acceptable to discard feedback if you believe you have a richer source of information that validates what you are doing is a better course. We are intentional on feedback and borrowed a great framework from Netflix. 

Inspiring a Break Glass Mentality

Behavior change isn’t easy. Transformation isn’t for the faint of heart. Bulls aren’t for fine china shops. The software industry has been around for nearly 70 years and has grown to nearly a $500billion dollar annual market (Gartner). Along the way, a global network of distributors and value-added resellers formed. This channel helped software providers extend their customer reach, manage inventory, provide financial credit, deliver services, and more. But we are living in amazing times and the pace of change is unprecedented. Insert things like DevOps, consumption pricing, Marketplaces, product-led experiences, and community. The way buyers discover, try, procure, deploy, and operate software solutions is changing…and changing fast. It’s time that sellers (ISVs) get more nimble as well or they will be left behind. 

For startups, no worries, embrace digital selling right out of the gate. If you have been around a while, this will require change, and that change will leave glass on the floor. Appoint an executive champion, a Chief Cloud Officer, who has the smash in the organization to work across sales, channel, marketing, finance, legal, operations, etc, and give them the power to impact change. The existing go-to-market machine must continue to run while you explore, build, and execute on your Marketplace journey. Tackle is here to be your guide with the experience and learning from doing the same with hundreds of others companies on the same journey.


Bias for Action

One great thing about being back in a high-growth startup is the incredible bias for action. Iterate, pivot, minimal viable product (MVP), there are all sorts of buzzwords to describe the new mentality to building the next generation of products. At the end of the day, it comes down to action. Make decisions, take actions, fail fast, double down when things go well. At every step validate with customers and partners. This lives throughout the organization at Tackle. We have empowered our team to act and we have nurtured an environment where failure = learning. We embrace new talent in our rapidly growing organization with efficient onboarding, strong leadership, and trust. That leads to people jumping in with a sense of belonging and a sense of responsibility. That leads to action. You can’t hide in a small company, you can’t coast. And in a remote-first company, you can’t be “part of the furniture.” In my mind it is OK to be content in mind and soul but not in passion. 


Finding My Hedgehog

When I was making the move to Tackle, a business colleague said, “Are you really going to leave your cushy corporate job, big title, and fat salary to gamble on a startup?” I disagreed with elements of that statement, but I understood the spirit. Better said, “Are you really going to walk away from a great company where you have established a great career for something a lot less certain?” Either way, my answer was yes. In Tackle, I found my hedgehog. If you aren’t familiar with the concept take a look at this article from legendary business author Jim Collins. 

Over the past 5+ years, I developed an incredible passion for changing the way sellers sell and buyers buy software. I have the battle wounds and the victories and want to use those experiences to help shape an industry, not just a company. I believe we are in the very early days of an incredible transformation in software go-to-market and procurement. I believe the intersection of these things is right where I belong.

Go find your hedgehog! And if you think it might be at Tackle, we are hiring 🙂

Simply Get Listed & Start Selling