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

Maximize Sales: How to Develop a Winning Spirit

Maximize Sales: How to Develop a Winning Spirit

Super Bowl LI is set to take place this weekend with our Atlanta Falcons taking on the Patriots. It’s no wonder we’re in the #WINNING spirit here at SalesWise! Believe it or not, sales organizations work much like sports teams. No, you’re not running the field and tackling 200-plus-pound men. But, you are tackling other big challenges in the marketplace, among your competitors, and maybe even within the walls of your own company. A sales leader is much like a coach, guiding his team towards the win. But, how do you ensure you have the right winning spirit?

Step 1: Use #WINNING Words.

We know sales can be tough. Some days you’re up and others you’re down. One of the biggest keys to cultivating a winning spirit for your team is to continuously use winning words. Though the numbers may be low, it’s about looking ahead. The team may have lost the last three games, but to win, they must look forward and never lose faith in their ability to win. As a sales leader, you should point to the positive and/ or the progress you and your team are making. Be sure to devise a plan to keep your team moving forward.

According to Wayne Goldsmith, a sports coaching consultant, effective motivation is a lifestyle, not a one-off speech or promise of gifts or money. Sure a bonus can go a long way as a motivator, but that prize may be a ways off (e.g., end of the quarter or year). Instead, focus on the positive culture you are creating day-in and day-out to inspire optimism and self-motivation for your team. Do you have 50 yards to go, or do you only have 50 yards to go?

Step 2: Have Skin in the Game.

Let’s get real for a minute. Whether you realize it or not, you already have skin in the game. As a sales leader, your success is directly related (probably wholly dependent) on your team’s success. So instead, the real question is: does your sales team feel like you’re in the game with them? Or, just standing on the sidelines?

How do you lead while also allowing your team to feel like you are one of the team? It’s a fine balance for sure. There are some measures you can take. Ask yourself, “What am I doing to personally communicate my commitment and ambitions to my team?” Some of this may be verbal, but much may also be non-verbal. When your team stays late, do you stay late too? Every company is different; so, think about your organization and the ways in which you may show your team you’re in it with them.

Step 3: Always be #WINNING.

You’re probably thinking, “Sure, easier said than done!” But to always be winning does not mean that you’re always “scoring” great leads. Rather, it’s about taking a winner’s approach to every task. New York Times best-selling author and business coach, Suzanne Evans, said it best with her book, “The Way You Do Anything Is the Way You Do Everything.”

In sales, there are no off-days… no losing moments. The attitude of each of your team members must be to always do every task to the best of their abilities. As the sales leader, you must also recognize that abilities are never equal. Be attuned to the subtle differences between “involved” team members and “committed” team members. An “involved” team member will participate in the task at hand. A “committed” team member will dedicate themselves to the task at hand and seek to perform it at a higher standard than what’s required.

Set small goals for your team. Achieving these smaller targets can provide focus and motivation in their day-to-day operations. Over time, the cumulative effect of setting and achieving these daily goals can be significant and lead to greater success. Consider the Olympics. For Olympic athletes, it’s not every four years; rather, it’s every day (W. Goldsmith).

No, you’re not seeking touchdowns and field goals in the 51st Super Bowl, but you are pursuing leads and new customers. How you get there is entirely up to you. Developing a #WINNING spirit is a must and committing to the relentless pursuit of improvement is also most valuable.

For the Atlanta Falcons, we hope that belief brings a win this Sunday. For your team, we hope that means you’ll venture to learn more about SalesWise’s Business Relationship Intelligence by visiting #RiseUp


Sales at a Stalemate

Sales at a Stalemate?

It’s still January and though you have set your sights on a banner year, your sales pipeline may be telling a different story. Why is it that sales seem so much harder these days? And, how can your sales team cut through the noise to create meaningful connections and successful sales?

Finding the Connection

With advancing technologies and growing corporations, the sales cycle has become even more complex. Where sales used to be one-to-one, now most B2B buying decisions involve 7-8 people (Gartner). That’s a lot of decision makers! How can you possibly make all the connections?

Traditionally, connections are tracked in your CRM system. However, with growing contacts, the feasibility of updating all those records becomes wholly inefficient for your team. In fact, today’s sales professionals update an average of 60 CRM records a day, and only spend 33% of their time actually selling (Toutapp)! There’s a need for a better way.

The reality is that much of sales relationships are fostered through your sales team’s inbox. Whether that’s an email, meeting, or shared document, a lot is taking place in the space between your team’s individualiz inboxes and CRM database. That’s why, with SalesWise, sales professionals discover an average of five times more contacts.

An essential step in creating meaningful connections is to first identify all those connections. Don’t get lost in the space between.

Making the Connection

Thank goodness you now have all the cards and players before you. But, what now? How do you make that connection meaningful? You’ve likely heard it before – as Entrepreneur recommends, you have to help your prospect buy rather than simply trying to sell to them. According to CSO Insights, sales teams have a 56% greater chance to meet quotas if they engage a buyer before that buyer is contacting the seller.

That requires your team to get curious. Ask your prospects questions, and work to build more personal connections. Access to data will become even more crucial as you work to anticipate your prospects’ needs and respond to them preemptively.

Business Relationship Intelligence (BRI) allows for full-access to critical data unencumbered by traditional per-seat licenses. Just as your contacts externally have grown, so have your internal contacts. With SalesWise, there are no limitations on who can access crucial customer data. Strategic collaboration between your sales team, marketing, finance, procurement and other functions enable more capable responses to prospects and customers – which, in turn, leads to more successful sales.

Don’t let sales get stuck in a stalemate. SalesWise offers sales leaders 300% more visibility into your team’s relationships and interactions with prospects and customers. Know everything. Be prepared for anything.

Learn more about SalesWise’s Business Relationship Intelligence platform by visiting

5 Essential Skills of a Great Sales Leader

5 Essential Skills of a Great Sales Leader

The role of a sales leader can be challenging – managing teams, projecting sales, enabling and sustaining a stable (and hopefully successful) sales process, and more! The job description is clear. Your role is defined. But, what skills really set the great sales leaders apart from the rest of the pack?

1. Strategic

Every great sales leader must be strategic. In a position where you are constantly reviewing data, plotting an approach and predicting an outcome, it’s crucial to be not only analytical but also investigative. It requires the ability to recognize patterns, tune into trends, and seek out the necessary insights.

Data is central to these points, and thus, must be readily available to you. CRM systems can provide some of the data you need, but in most cases, sales leaders are also pulling data from alternate teams/ resources, as well as anecdotal insights from their sales team members that never made it into the CRM system! If there is a problem to be solved, a hurdle in your team’s pathway, you’re the leader to figure it out. Devising the how-to plan isn’t even possible unless you have the most efficient tools to do so. A leader recognizes this challenge and will approach a solution strategically.

2. Innovative

According to GE’s 2012 Global Innovation Barometer, 92% of senior executives agree that “innovation is the main lever to create a more competitive economy” ( The ability to innovate is a vital skill. In an industry that’s about as old as they come, it can be hard to think outside the box and reinvent a new and better way.

Great sales leaders are always looking for a new way to do things better. By nature, they are receptive and open to untried methods that may afford them greater efficiencies and growth – that competitive edge.

CRM has been a cornerstone tool in just about every sales organization. With new technologies abound, maybe it’s time to think outside of the software box. SalesWise is an innovative Business Relationship Intelligence platform that provides sales leaders with real-time data synchronized across all their systems to provide a full 360-view of customer interactions.

3. Communicative

Having a strong, innovative plan is great and all, but if you can’t effectively communicate it with your team, you go nowhere. Communication is essential in any managerial role, but to a much larger extent in a sales leadership role. Relationships both inside and outside of the organization carry great weight. Insight into customer interactions is important, but so are insights into inter-departmental interactions. 80% of line-of-business leaders in sales, HR, procurement and more say problems arise due to different internal systems/ applications that do not talk to each other (IDC). It’s clear siloed structures are a challenge.

Collaboration is the brother to effective communication. 86% of employees and executives cite lack of collaboration or ineffective communication for workplace failures (Salesforce). It’s fundamental to a sales leader’s role. Successful sales models employ not only a smooth process, but also equal collaboration between both sales and non-sales team members alike. Data limited to CRM licensed users and/ or an individual’s inbox makes collaboration an uphill, time-consuming, and costly battle. That’s why SalesWise believes in democratizing your data to facilitate communication and office-wide collaboration.

4. Effective

In a personality test, top sales managers scored 27% higher in the priority-focused facet than underperforming sales managers. To be effective, sales leaders must be good at identifying and tackling the priorities. They’re impactful – seeing the big picture and discovering the one solution that can make it better. In fact, high-performing sales leaders are 51% more effective, on average, in meeting their quota goals than their underperforming counterparts (Harvard Business Review).

So, how is this possible if, sales team members only spend about 1/3 of their time selling? What else could they be doing? The rest of the time is spent on administrative tasks (e.g., CRM data entry), meetings, and research. What if you could increase sales productivity by reducing the need for data entry, catch-up meetings, and customer insight research?

SalesWise’s proprietary Cross Application Relationship Data (CARD) platform enables visibility into every vital conversation with prospects and customers, meetings occurred or upcoming, documents exchange, and every person involved in a sales relationship. Everything aggregated into one simple, always up-to-date view. By just checking the CARD, sales leaders and their teams can share real-time critical intelligence across the enterprise while more effectively managing their sales relationships. Talk about impact!

5. Motivational

Lastly, every great sales leader must be a motivator! As the late and great Muhammad Ali once said, “It isn’t the mountains ahead to climb that wear you out; it’s the pebble in your shoe.” A sales leader’s job is to minimize the pebbles for his team.

Coaching is the number one sales management duty that drives sales performance. 69% of salespeople who exceed their annual quota rate their sales manager as being excellent or above average (Harvard Business Review). A great sales leader is a great coach who inspires his team to reach their greatest potential. Challenges to a sales team’s productivity, data accessibility, and integration are all pebbles in the sales process. To motivate, great sales leaders must eliminate these stones.

Aristotle once said, “The whole is greater than the sum of its parts.” Behind every great sales leader is a team of great sales people. Together, you are stronger. The right tools can help to set you apart. To learn more how SalesWise’s Business Relationship Intelligence platform can enable sales leaders, visit