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

Four Signs that Account-Based Selling is Right for You

Four Signs that Account-Based Selling is Right for You

One of the biggest sales strategies in 2016 was Account-Based Selling (ABS), and 2017 has been building on its momentum to drive today’s B2B sales. With the breadth of channels and depth of information sales and marketing teams have access to, gone are the days of “any lead is a good lead.”

Account-Based Selling has grown due to the strategy’s effectiveness in breaking through the noise surrounding digital marketing. While in the past there may have only been one or two decision-makers within the buying process, Gartner found that now 7-8 people are typically involved in all areas of the buying process, especially in enterprise tech sales. This buying process calls for a solution that engages with multiple functional groups within a single organization, rather than addressing a singular buyer persona.

According to the 2016 #FlipMyFunnel Account-Based Marketing Benchmark Survey Report, 64% of B2B marketers who don’t currently have an account-based marketing program plan to implement one in the next year.

Is your organization ready to take the plunge into ABS? If you’ve seen the following signs, you’re ready to make the strategic switch.

You know your target audience

This probably sounds like a no-brainer, but the first step to implementing an Account-Based Selling strategy is knowing the key accounts your strategy will focus on. According to the 2016 B2B Marketing Data Report, 75% of records analyzed lacked the necessary data on prospect industry, revenue, and employees crucial to effective ABS. The foundation of ABS is that your sales and marketing efforts are focused on the account at large, rather than a specific job role (“persona”) within an organization.
Furthermore, ABS is built around quality over quantity – if you don’t have a precise knowledge of your target audience, ABS as a strategy will be ineffective. With the traditional funnel, the top of the funnel is filled with as many prospects as possible. ABS, on the other hand, engages fewer accounts, but they are much more targeted and representing the ideal customer profiles (ICP) with a higher likelihood to close.

You’ve exhausted your inbound marketing strategy

This isn’t to say that inbound marketing is dead, by any means. But the B2B ecosystem is incredibly saturated, and may not be the most effective for your target market in 2017. With a market that is moving towards a group-buying process, inbound marketing loses effectiveness because it is difficult to consistently produce messaging that resonates with everyone (FunnelEnvy). A strategic combination of inbound marketing and ABM will establish your organization as subject-matter experts, while delivering highly-targeted content to those accounts deemed most important.

You have strategic, valuable content (Or, you’re ready to create it.)

If you’ve been using an inbound marketing strategy, it’s likely that your organization will already have some valuable content that can be tweaked and expanded upon. But remember, the success of ABS relies on attention to detail for an entire organization – not just the champion (or at least, the target personas targeted within the account).
This presents an opportunity for perfectly crafted content that speaks to the specific problems and needs of each point of contact. While your old content marketing strategy may just speak to the problems of a specific user, you may now be reaching six different functional roles within one organization.

True sales and marketing alignment

In an ideal world, an aligned sales and marketing strategy would be the industry norm, but that isn’t necessarily the case. Sales and marketing alignment are critical to an ABS strategy. Misalignment, then, inevitably leads to failure. Organizations with aligned sales and marketing teams are 67% better at closing deals (Marketo) and generate 208% more revenue from marketing efforts (MarketingProfs). In fact, Account-Based Selling and Account-Based Marketing can almost be used interchangeably – the process relies heavily on the collaboration of the two teams. This is because sales typically owns the account relationship, while marketing is generally responsible for the messaging and branded assets. In order for sales to provide the most valuable content available to their highly-qualified targets, they need to collaborate with the larger marketing initiatives.

Enacting ABS is no small task because it requires a fundamental change in mindset – both in your sales team and by your sales leadership. Clear communication and accurate forecasting to organizational leaders are imperative to the success of ABS. But when the signs are all present, account-based selling can be one of the most effective ways to land large accounts and expand within them.

Learn how SalesWise can provide greater visibility to your sales leaders and drive additional incremental revenue when shifting to an Account-Based Sales strategy (see how it works). Or, schedule a quick demo to see how SalesWise enables ABS teams.

Understanding Your Customer’s Needs (Before They Know They Need it)

Understanding Your Customer’s Needs (Before They Know They Need it)


As one of the oldest professions, there have been many philosophies through the years about how to sell more effectively. While it’s not a new concept to sell to a customer based on their needs (e.g., solution-selling), it is a relatively new concept to sell to a customer based on the needs they don’t yet know they have. This is better known as insight-selling.

Here are five key components sales leaders should look for in understanding their prospective customers’ NEEDS:


Every business has a unique roadmap. It’s the way in which they carry out the core functions of their business. Before your sales team picks up the phone to cold call a prospect, it’s imperative that they understand the nature of the customer’s business and the innate needs that customer may have. When asked, only 13% of customers believe a sales person can understand their needs (The Brevet Group). Not doing your homework is one thing. The reality is the data is likely already there. Work with your company across divisions to share your collective insights into the necessities of these customer targets. It’s not likely they would ever even be on your list of prospects if you didn’t have an initial understanding of their core business needs.


It takes a wise guy to know a wise guy. As expert Wise Guys, we understand the need (and pressure) for business leaders to show innovation and enterprising qualities on the job. Perhaps the most important factor in selling to a customer before they know they need what you have, is understanding this need for the customer to be the discoverer.

Yes, you reached out, but it’s the wise customer who was resourceful in discovering the advantages they may bring to their organization through your product or solution. Allow your customers to show the initiative within their company. The decision is rarely left with one individual alone these days. In fact, on average, 5.4 people are involved in today’s business-to-business purchase decisions (CEB Global). By allowing your prospect to show his/ her enterprising nature, the customer, in turn, becomes the champion for your solution among the many purchase decision-makers.


Another key need for the successful champion is to clearly and simplistically outline how your solution can be effectively implemented. Sure, you know the plan, but to effectively sell it, you should put your customer in the driver’s seat and give them the “race car” experience. Allow them to feel the speed, the wind across their face, and the exhilaration when they cross the finish line. Depending on your business model, this could look as simple as a detailed case study or customer testimonial from a similar industry or it could be as hands-on as a demo or trial program. Remember: talk is cheap and seeing is believing when it comes to effective sales.


Keeping with the race car analogy, the car is on the track, but we all know this isn’t just one race. Selling to a customer involves understanding their need for direction beyond the first lap or test drive. In many cases, this could be the need for projections or ROI. Clearly defining and demonstrating how your solution or product will help their business to grow and gain trajectory over their competitors is a crucial step. It’s what ensures quality and sets the foundation for not only a more immediate sale, but also a long-term, trusting sales relationship.


Finally, the last factor you should never overlook when it comes to understanding a customer’s needs is their need to sell! How will your product or solution enable them to sell? This could be a direct sell in terms of a solution that furthers their operational structure. Or, it could be a metaphorical “sell” in which a sale is equal to their company’s definition of success or end goal. Consider how your solution or product will be used within the core functions of their business and be proactive in communicating how it will enable a win for their business.

Selling to a customer before they are even shopping for your solution or product (i.e., insight-selling) requires access to insights. Business Relationship Intelligence (BRI) offers companies and sales teams alike critical insights into their customers’ needs and experiences in order to effectively sell and build a positive sales relationship. Learn more at

SalesWise Sales Game

Three Signs It’s Time to Up Your Sales Game

Everyone knows you have to have “game” to close deals and solidify the sales relationship. But what should you do if your sales have slumped and solid leads are coming in at a snail’s pace? There are many reasons performance may be temporarily lacking. Here are three telltale signs it may be time to up your game:

Sign #1: You’re struggling to get updates from your sales team.

Your team works hard. Inevitably they feel inundated by the amount of data entry they need to complete while also ensuring to spend adequate time selling. In fact, sales professionals spend only 33% of their time selling (Toutapp). They spend an average of four hours per week updating Salesforce. The reality is, you’re not alone. Yet, Salesforce itself reports that 91% of CRM data is incomplete.

Therefore, do you spend time motivating, inspiring, incentivizing, or maybe even antagonizing your team into completing their CRM updates? Or, do you look at the real dilemma? Truth be told, what you really need is greater visibility. Your CRM solution is only as useful as the data it holds. If most of the data is incomplete, you need to look elsewhere. The real relationship-building is taking place outside of your CRM. Instead, it’s in your team’s inboxes. It’s their email communications, the meetings on their calendars, shared documents, and more. Transparency breeds more effective sales outcomes – time to get wise!

Sign #2: Productivity is a never-ending challenge.

A wise guy once said, “Don’t be busy, just be productive.” So, what’s keeping your team busy?

Part of it may be the CRM data entry we just talked about. Another part may be all of the other disparate systems your team is utilizing. IDC reports 61% of employees typically access four or more systems to get the information that need to do their jobs. Moreover, in their 2015 Workforce Transformation Survey, they additionally reported that employees spend an average of 7.36 hours per week trying to find information and an average of 8.15 hours per week trying to find people or experts.

Other productivity killers? When asked what gets in the way of work, employees say wasteful meetings (59%) followed by excessive emails (43%) (Workfront 2016 Survey). Perhaps it’s possible that in your best efforts to increase productivity and the flow of information – through regular status update meetings and/ or a continuous trail of CC/ forwarded emails – you may, in fact, be enabling a less productive work environment.

At SalesWise, we resolve common sales productivity issues with our proprietary Cross Application Relationship Data (CARD) platform that aggregates all of your sales relationship data into one simple view. In turn, you reduce the need for recurring sales-update meetings and decrease email workload by 30%.

Sign #3: You feel like you’re on an island.

In today’s corporations, it’s impossible to achieve effective sales without the efforts and collaboration of other interdepartmental groups (e.g., accounting, procurement, legal, etc.). According to a 2005 study by McKinsey, only 25% of senior executives surveyed described their organizations as “effective” at sharing knowledge across departmental boundaries.

Equally important to your external sales relationships are these internal relationships taking place within the walls of your organization. Truth be told, when divisions are siloed, so is your data. As long as your team feels like it’s on an island and/ or communication with these departments is cumbersome, lengthy, or worse, ineffective, your sales may suffer. In fact, 86% of employees and executives cite lack of collaboration or ineffective communication for workplace failures (Salesforce).

At SalesWise, we believe in democratizing your data as a means of driving stronger, more effective alignment and collaboration. No matter how your team or customers change, all of your relationship data is organized and instantly accessible to those who need it most – whether on your sales team or in the marketing department.

Merriam-Webster defines “game” as “a procedure or strategy for gaining an end.” Whether in a slow season or at full capacity, your team should feel ready to take on the challenge without concern that opportunities or contacts will fall through the cracks. Learn more about SalesWise’s Business Relationship Intelligence by visiting