Reflections: Pay attention to what your failures are teaching you

Throughout December we will be sharing Reflection stories from some of our Qualtricians. These stories reflect on the last year and beyond — recognizing the good and the bad, the struggles and the successes. Today we are featuring a story by Steve in Enterprise sales and his last ten years at Qualtrics. 

In September 2022, I hit 10 years at Qualtrics.

I was doing some reflecting on my time, from starting as an intern, to moving through the account executive ranks, to sales leadership, and now as an enterprise account executive in our healthcare vertical. 

There were a lot of different phases I experienced joining the company after our Series A in 2012 with 250 employees — through an IPO turned acquisition, then an actual IPO years later, through mergers and acquisitions. I’ve broken down some of my experiences and learnings into these blocks. 

The Early Years

The Good Years

The Down Years (Personal)

The Consistency Years

The Struggle Year

The Accelerator Years

The Early Years

For the Early Years here's two things that stick out.

Scrappiness - I started when we had 250 employees, I was given a Salesforce login, a phone, and was told to call professors and deans about our survey software. Not a ton of training, but trial by fire taught me a ton.

50-60 dials a day (or more)

Once I left a voicemail to a dean of a university.

I went into my usual spiel, then entered autopilot (I don't recommend this)

Right as I hung up the phone I realized what I had ended with...

"K, love you, bye"

Enter mortification.

All the other interns got a good laugh out of it.

Later that week we did our company wide meeting where we shared Whoops moments.

Myself and two others shared ours. Mine was voted the best Whoops moment.

So I got the silver trophy with the purple monkey on my desk for the next week.

In the early days, it was really important for us to recognize that we make mistakes and fail sometimes. It's not so much about the mistake as it is learning from it, and all of us can learn from others, not just ourselves. This proactively helped us to fail fast and get better.

The Good Years 

It all started with being asked to demote from an AE to an SDR.

It felt like the death of my early AE career.

I said no, and was placed on a new team thanks to Austin Bankhead advocating for me.

That next quarter I billed enough to secure my first promotion.

Over the next 12 months I was promoted twice more.

It was slingshot growth.

I went from being asked to take a step back to being promoted 3 times in 18 months and more than doubling my earning potential.

Learnings (if you got this far):

• Rocket ship - we doubled the company size each year.
• Alignment - Customer, Company, Team, and Individual could all be successful together - not a series of cascading win-lose scenarios.
• Ryan Smith used to say "get good" and everything else would follow. If you nailed your role you would be given the opportunity to scale or take on something more challenging.
• Learning to operate within ambiguity and structure leads to opportunity. The ambiguous times can be hard, but if you figure it out that is where the biggest growth happens.
• My focus on getting good led to really thinking about personal development. I started to break it out each week with a 30 minute to 1 hour session per day. Break it down into percentages: 40% of my time learning the product, 20% of my time learning the industry, 40% sales acumen.
• I worked with some of my favorite people in this phase. Ryan Fowler, Todd Marchant, and Shane Stephenson, AIA to name a few. People make work fun.
• Never underestimate the power of a personal brand. The Sales Operations Director went to bat for me even though I barely knew him because of what he had seen in my metrics and what he had heard about me.

The Down Years

I missed for 6 quarters in a row.

After slingshot growth and promotions, I failed…hard. I took the focus off of my book and individual goals to help others and neither succeeded.

After missing the last half of 2015 I proceeded to miss each quarter in 2016 — with the most painful quarter being Q2 2016.

I missed by $9k after closing 26 deals. 

This led me to a realization — I needed help to grow my deal size and work on bigger problems for organizations.

I had one leader that offered to help with their time, but that wasn't feasible due to their time constraints.

I had another leader give me homework then set up 45 minutes to dive into it.

After doing the homework I learned several things:

• All my deals were similar products (usually one not multiple).
• Conversations happened at the same level (usually manager, rarely director).
• I wasn't being consultative or prescriptive.

I came out of the meeting with those 3 actionable steps for me to focus on to help organizations with bigger problems. Talk higher, start with more than one product, and be more consultative/prescriptive.

In Q3 2015 and Q3 2016 I managed to lose two of the bigger deals of my career on the last day of the quarter. I learned you cannot, as a rule of thumb, live off of just big deals — it introduces risk and volatility into your KPIs. Even when it gets busy, it's important to generate more pipeline, it makes you easier to work with not just internally but *externally* for your customers and prospects.

The loss in Q3 2016 stung and stuck, in Q4 I learned my lesson, had a big RFP come in that normally I would have dropped everything for those two weeks but instead I forced myself to prospect first so new projects were still the focus, then used the rest of the time for the RFP. It led to some busier weeks but that prioritization helped me enter the consistency years (right when I needed it the most).

Longest story short — pay attention to what your failures are teaching you. They'll be some of your best teachers if you let them.

The Consistency Years

After consistently missing for a year and a half I learned some things that set me up for consistent success just when I got the busiest.

• Pipeline — just like an apple a day keeps the doctor away, I learned that small consistent efforts to generate new conversations (prioritized daily) lead to a more productive mindset and keep things more interesting because it is often a little uncomfortable to strike up new conversations.

Also pipeline solves so many problems for you as the sales rep and for your customers. When you have plenty of pipeline, you and your customer can align on a more appropriate timeline that is convenient and helpful for them and less so contingent on your own business requirements.

• Features are not the way to go. Knowing your product like the back of your hand is great, but don't let it be a handicap. Knowing why it matters, what problem it solves, and how that problem not only makes life easier for your customers but how it impacts their business will change your relationship in deal cycles and beyond.

• If you are talking to the same level of people in each organization you are often missing layers of detail or vision that will come back to bite you, losing to the status quo, or missing out on transformations.

When I put these learnings into place I didn't miss a quarterly number for 3 years, I was promoted twice, and was the #2 AE in the organization while getting my MBA from Duke and traveling internationally once a quarter.

The consistency years wouldn't have **stuck** without the down years where I had to learn these lessons over and over before they stuck.

The Struggle Year

2020 turned things on its head. I had just grown my team from 0 to 10 people and split the team into two teams to focus on our growth. 

The team that used to be in-person every day and never had done consistent remote work just got locked down and sent home.

People were struggling with mental health because most couldn’t even leave their homes. 

Sales were taking a backseat because of very real personal issues.

I learned a lot:

• People process challenges differently. Help manage them in a way that leads to their strengths.
• When life is hard, simplify. Giving clear, communicated expectations on what good looks like when there is so much uncertainty gives its own sense of peace. Control what you can control and remove uncertainty where you can so there is less of a cognitive load on you and your people.
• Focus on execution — even with an incredible amount of change, our team pulled in the biggest deal of the year which took a huge team effort and one rep who really dreamt big.

It was my first missed year in 3 years but a respectable finish. At the end of the year, so many of my reps wanted to find a way into leadership roles which were few in our small but growing department. This led to my next phase.

The Accelerator Years

I made a pivot.

After moving into sales leadership for 3 years and growing my team from nothing to 3 teams, I was asked to consider a pivot to a new team that was starting in our enterprise healthcare division.

It was new, a little risky with a new-to-the-organization manager, and one of the best decisions I have made career wise.

Reasons to make a pivot and how to lean into ambiguity and change:

• Do enough of your homework to know what the opportunity is, but not enough to question everything. I found that having eyes half open helps me go beyond a gut check without entering analysis paralysis.
• Think of the manager you will work for, your individual opportunity, where it sits within the organization, and what customers you’ll get to work with. Remember the good years? When incentives are aligned as much as possible across customer, company, team, and individual - things are FUN. 
• Bet on yourself and put in the work. It’s the little things you do day to day that will shape your ability to climb the mountain. 
• Lastly, I considered the value this pivot might have for my team. So many of them wanted a leadership position and me taking on a new role opened up a leadership spot immediately so one of them could get the opportunity. 

The last few years have been navigating a ton of change which tends to lead to ambiguity. One of my previous sales leaders used to say, “ambiguity breeds opportunity.” If you have the skills to navigate ambiguous situations, you have a higher likelihood of turning those into gains for you and others.

These last two years have catapulted me into a next tier experience that I’m grateful for. That same sales leader would always remind us, “gas pedal is on the right.”

So the gas pedal is on the right, welcome to the accelerator years.