sales team coaching

Teaching A 25-Year Sales Leader New Tricks: Joining SalesWise As The New CRO

As of tomorrow, I will have been with SalesWise for 60 days now — joining as the Chief Revenue Officer. What a ride it’s been, and I am sure, will continue to be!

In the past two months, I’ve seen a lot and have learned a lot even with 25-years experience leading teams under my belt. I’ve had the opportunity to hear from clients the top challenges they face in leading their sales organizations. I’ve learned that the leadership challenges I’ve struggled with the last few years are far more common than I thought and that the world is changing more rapidly than ever as the Information Age reaches maturity. I’ve also had to fundamentally rethink the way I lead a sales team.

It’s been a privileged position. To be able to speak to other sales leaders directly and hear their struggles and concerns has been humbling. It’s never been more difficult to guide a world-class sales function. And to see firsthand the value of what happens when a more complete view of selling efforts is made visible and transparent across a sales organization. This has forced me to rethink and retool some of my most deeply entrenched sales management strategies.

I thought I would take a moment to share what I’ve learned so far, focusing on three distinct lessons:

  1. Why I struggled ADOPTING the SalesWise platform initially, and how I adapted my style as a result of having more information at my fingertips.
  2. The CULTURAL difference I see here and in other companies that leverage the SalesWise platform.
  3. The ways I’ve improved my COACHING efforts as a result of having a deeper understanding of what is really going on with our accounts and opportunity pursuits.

Old Dog, New Tricks

“Check the card!”
“Steve, you can see it in the card.”
“Why don’t you just check the card, Steve?”

In the first two weeks of being a part of the fantastic team at SalesWise, these are the phrases I probably heard the most. It was really interesting. I joined SalesWise because I was very impressed and excited about the opportunity that rich data, with no data entry, could provide sales leaders and sales teams. I saw the huge potential and definitely wanted to be a part of it. Yet I struggled mightily to get used to the idea, and incorporate that rich and readily available data into my own approach.

As someone who has led sales teams for over 25 years, I came face-to-face with the notion that my management approach was grossly outdated and could be better channeled.

Over the first few weeks of taking my new post I ran the same pipeline update calls in the same way I always had:

“Daryl, what is going on with so and so?”
“Danny, bring me up to speed on the latest with ABC Corp.”
“How did that call with XYZ go?”

And my new team, thankfully, had one recurring response…

“Check the card!”

By that, they meant to check the SalesWise Card, where all their email follow-ups, meeting invites, documents exchanged and account contacts engaged were available and visible for everyone in the company. Myself included!

At first, it was a bit annoying. I didn’t WANT to have to check the card. I wasn’t used to having to check the card. Why can’t they just tell me??!! Then, it hit me like a ton of bricks. What they were saying was, “Steve, stop selling the Kool-Aid long enough to take a sip.”

As excited as I was to join the company, and as valuable as the tool seemed to me, it was interesting to see how engrained my old methods were. Methods, born of an age where this kind of rich detail was impossible; not even a pipe dream.

Thankfully, I powered through with the help of my team, and now I spend a lot less time asking what happened and more time strategizing, coaching, and offering to insert myself directly in a particular sales effort. I let my team do what they do best while enabling me to help them be their best. Our pipeline calls are more about deal strategy and next steps because objective reality is so plainly and easily seen. It’s been revelatory.

You can teach an old dog new tricks!

Sales Culture

One of the things I often get asked by clients is how SalesWise is received CULTURALLY; specifically by the sales teams whose activity is made visible to leadership and others so quickly and efficiently. It’s a very good question and one that needs to be considered closely before embarking on the path of radical transparency.

After thinking through my first 60 days at SalesWise and reflecting on some of my past career stops, the conclusion I’ve come to is this:

The SalesWise platform will ACCENTUATE whatever sales culture you have today.

If you have a positive, collaborative, and helpful management style and sales culture, SalesWise will accentuate that. If you have a domineering and distrustful culture, SalesWise will accentuate that, too.

I am thankful that the culture I stepped into here at SalesWise is so open, collaborative, and transparent. Is that a function of the people or the platform, or both? Probably both. The people here are some of the most committed and positive people I’ve ever had the good fortune to work with, and our CEO, Gregg Freishtat, rolls up his sleeves to do whatever it takes to make things happen. It’s a real team dynamic.

When our people are combined with the SalesWise platform – that gives our Marketing, Engineering and Finance teams just as much visibility as our sales team has – collaboration, transparency and teamwork are magnified. Everyone is pulling together to serve the client base and grow the business. When everyone can see the client through the same lens, personal agendas take second fiddle to the needs of the clients and the needs of SalesWise.

And I’ve seen the same dynamic with our clients. They report that after the initial adjustments, like what I experienced, teams work together better with SalesWise in place. Pipeline reviews are more honest and strategic. Leadership is more deeply and effectively engaged. Culture is magnified.

Coaching on Steroids

A recent report by SiriusDecisions looked at the top five challenges faced by Chief Sales Officers. It was interesting to see that three of the five issues were directly or indirectly related to coaching. Here are all five:

  1. What is the ideal organizational design and investments to hit my quota?
  2. How do I hire the right people and train them quickly so they can make an immediate contribution to hitting my quota?
  3. How do I improve sales rep productivity so I can get more business out of my existing reps, and how do I retain my best reps so I can hit my quota?
  4. How do I ensure that reps utilize a buyer-driven sales process so I can keep control of my business and bring predictability to the forecasting process?
  5. How do I work effectively with my peers in marketing, finance, and product so I can hit my quota?

At SalesWise, we believe that the keys to success are as follows…

Use a consultative approach that focuses on the buyers’ needs and priorities.
Connect directly with all the influencers and decision makers involved in making a purchase decision.
Bring the entire SalesWise team to bear in the effort to make the client successful.

…and we review these tenants regularly in our scheduled and ad-hoc coaching sessions.

From a leadership perspective, I monitor the messaging our sales team is using to make sure it is buyer-focused, not SalesWise-focused. From the emails and meeting agendas, I can drill into the depth of qualifying that has been done, and help my team think about how we map to specific business value in the unique client environment we have uncovered. My coaching here is focused on making sure we understand their business challenges and introduce ways the SalesWise platform can address specific and pressing business objectives.

I also use the SalesWise platform to graphically and intuitively see who we are engaging with and to make sure that the typical personas involved in the evaluation of our solution are actively and recently engaged. When I see opportunities to guide a salesperson, I am able to coach positively and point to wins where we had the right constituents at the table early and throughout the decision process. We use our industry-first Relationship Graph quite often to gauge whether the right people are being involved — it really is a game-changer.

And finally, I look for opportunities where a member of our Engineering or Onboarding teams can get involved to help answer client questions and resolve risk, security, deployment and other concerns. Like most sales teams, we rely heavily on the support of other teams to answer questions, address objectives and creatively solve unique client challenges. Getting these teams engaged at the right time is something I can impact by knowing the state of the opportunity and the kinds of concerns that are being raised by our client.

It has been a revelation how true transparency makes my coaching efforts more effective, while putting objective sales interactions front-and-center.

As I said at the outset, it’s been a lot of fun being a part of the SalesWise story. But it’s also been quite educational, even for a tenured sales leader. I hope you can learn from my experience and develop evolved management strategies; drive a culture of transparency; and coach and guide your teams more effectively.

If you would like to connect or discuss, you can find me on LinkedIn or