When and Why to Start a Win/Loss Program

I’m Ryan Sorley, Founder of DoubleCheck Research. I recently had the opportunity to sit down with venture capital firm OpenView, and one of their portfolio companies SmashFlyto discuss how they use Win/Loss Analysis to improve their decision making.

Competitive Intelligence

It’s fair to say most organizations have an anecdotal, or very cursory, understanding of what their competitors do for the most part. Public information through press releases, social media, or general marketing efforts is readily available. However, determining how to position your business against competitors can be pretty difficult, and very generic.

#WinLoss research starts with the hope that there’s something that you can walk away with, even if it’s painful to hear. When Josh Zywein, Vice President of Marketing started at SmashFly he knew they really needed to gain a deeper understanding of the business, and started by asking the question, “Do we track wins and losses right now? How do we track #CompetitiveIntelligence?”

The answer was “yes” from sales, but the reality was that most of that was done through self reporting by the sales reps, which can be very light on detail. A deal may be marked as a closed loss to a competitor, but there wasn’t much context surrounding why the deal was lost.

Some reps may dig a little deeper. Some reps may have good relationships with prospects, and aren’t afraid to ask why the deal was lost, or even what the business driver was for the selection.  “The reality was that even when that happened, we found that prospects would tell the rep what they wanted to hear, or would withhold detail that they might share with someone that’s a little bit more objective.”

Recognizing The Problem

Ricky Pelletier, Partner at OpenView, added, “Win/loss research can be eye opening. Seeing that juxtaposition is interesting, because you might start investing down one path of differentiation, when in reality the customer is buying you for a completely different reason. Understanding your value prop through the lens of the customer is incredibly valuable. Hearing it through the lens of a salesperson, or through marketing, is good, but it’s nowhere near as insightful as hearing it through the customer.”

From win/loss analysis you can expect competitive intelligence, understanding who you go up against, why you win, why you lose, and what resonates with a prospect in a particular deal against a particular competitor. When done correctly, and with purpose, a win/loss program can help align your sales and marketing strategies with your prospective buyers.

Zywein adds, “A company that is just crushing it from a sales perspective may not be worried about doing win/loss analysis. It’s not that they shouldn’t do it, but they probably have fewer problems than companies that are willing to make this investment. First is recognizing that there’s a problem somewhere, or something isn’t working quite as well as you expected it to.”

Perception may be part of the problem. A lot of companies have the belief that they understand their customers really well, especially when the leadership team has been involved in the selling process. As they move from being the ones selling to having more of a broad-based sales team and getting less direct intelligence, there is sometimes a disconnect between what they know, and what they think they know. They’re just not sure how much new information they’re going to learn from win/loss research, because they perceive that they have a really close relationship with the customer.

Access To Insights To Make The Right Decisions

Most of the win/loss data and programs that OpenView has run have been done by their internal team. They don’t push their portfolio companies towards win/loss research because it’s good for them as the investor. Their goal is to show their portfolio company the data so that they can make the right decision to benefit the company, which is ultimately good for everyone involved.

OpenView is a minority investor, and as Ricky Pelletier said, “There are reasons why we have a lot of faith and excitement about a company. Whenever we do loss reviews, and identify painful information, the mindset is not to attack the company, or talk about all the things they’re doing wrong. We’re still really bullish about the prospects, and there’s a reason why we made a bet on that company.” When any areas of improvement are found, it is tempered with the fact that OpenView has made a commitment and is excited about the investment.

With close relationships between OpenView and their portfolio companies, there couldn’t be better alignment behind getting the right answer.

When OpenView Offers Win/Loss Analysis

OpenView operates something like an outsource agency, or a consultancy, for win/loss analysis. It’s offered when value is recognized by both OpenView and the portfolio company.

Kyle Poyar, Senior Director of Market Strategy at OpenView shares, “Generally, there’s a certain trigger behind the research. For instance, if a new competitor just raised a lot of funding, they’re coming out, taking some market share, winning some deals that you thought would be natural for you to win or if you’re launching a new product line. There are certain triggers where we say it really makes sense for you to start collecting some of this information from your buyers.

Closing Thoughts

Give win/loss priority. Delegate resources to ensure success. Act on the input. Recognize that success doesn’t happen overnight. Your customers and your prospects are some of the most valuable data sources that you have. You want to be very careful with how you use that, and how you treat those relationships.

To learn more, please visit: https://www.linkedin.com/pulse/when-why-start-winloss-program-ryan-sorley/

Unleashing the Power of the Sales Playbook


I’ve seen many variations of sales playbooks in my career. From the simplistic and overly-general to the content-dense with loads of long lists, hyperlinks, and prose. Playbooks are typically too long, too complicated for the user, and out dated immediately after publishing.

“It’s a boat anchor, weighing down our 
sales teams rather than empowering them”

All too often a document that is intended to help a sales rep quickly prep for a call or meeting turns into a compendium of everything that is known about a product, its features and differentiators, the marketplace, the target audience and the competition. It’s easy for this sales tool to turn into sales overload. It’s a boat anchor, weighing down our sales teams rather than empowering them.

Instead of wasting time and money creating a document that the sales team won’t use, let’s focus on what the sales playbook is intended be. A valuable sales playbook—one that will actually be used—will satisfy three goals:
• It will provide relevant information at the right moment in the sales cycle
• It will be quick and easy to access
• It will be kept up-to-date

Here are three tactics to ensure your sales playbook reaches all three goals and becomes a tool that sales people will love. (Don’t forget, while pulling together the information that will go into the playbook, to follow the advice of the best chefs and fashion designers: edit, edit, edit!)

Tactic 1: Make it relevant
In today’s world, buyers are self-educated. They are often quite far down the buying path before they ever engage with Sales. Rather than assuming the interaction starts at the beginning of the sales cycle, focus the playbook on how to deal with prospects who are already halfway to a decision. In concrete terms, this means equipping the sales team to uncover specific needs, position the solution, clearly articulate the value proposition, and help the buyer build a business case.
Keep information focused: this means avoiding the tendency to include too many personas or spend time coming up with cutesy names. Rather, it means providing a clear explanation of the problems, attitudes and concerns of the most likely buyers. Create two or three personas with the clearest fit, and make explicit assumptions about where they are in the buying process. Discuss what criteria are most important to them, what value propositions are most relevant, and what influences them. Make sure to include a least one key decision-maker in the mix. Validate by mining your current database, then following up on clues by using questionnaires, surveys and interviews to find the most relevant answers for these key issues. As the sales team works through opportunities, they will be able to gather new information that can be used to keep personas and value props updated.

Tactic 2: Make it accessible
We are all slaves to our devices. Who doesn’t live in email all day long, respond to every ping of the smart phone or check social media at all hours of the day or night? If this is the reality, why do we give our sales teams paper printouts, lengthy presentations and cumbersome documents where it’s difficult to find needed information quickly?
A good playbook is one that is used frequently, both in preparing for the call and while conversing during the call. That means a playbook that is easily accessible, and that is easy to navigate. While the basic work of assembling the information for the playbook will not change, our method of providing that information to the sales team can take a dramatic turn for the better if we use tools to bring the playbook to life online. Today there are a number of tools that let you produce highly interactive sales playbooks, so your reps can find exactly the information needed with just a few clicks. Whether it’s market-specific customer references, online demonstrations of functionality, ROI calculators or competitive knock-offs, an online sales playbook can be a wealth of information when the sales person needs it: now!
One bonus of a well-constructed online sales playbook: the reps can enter feedback while they are online, the fodder for the final tactic – making it a living document.

Tactic 3: Make it evergreen
As sales learns more about who buys (and doesn’t) and why, the sales playbook can and must change to incorporate new learnings. Similarly, as product features and functionality evolve, as new products are introduced to the market, as new competitors come onto the playing field, the sales playbook needs to be a living document that can accommodate the changing reality.
Plan for this. Budget for it. The sales playbook needs to be updated consistently with the latest messaging, positioning, competitive analysis, market trends, personas and products, and value propositions as they become more finely tuned. Don’t forget to advertise any significant changes to the sales playbook to your direct and channel sales teams. Give them a reason to keep coming back for more. And don’t forget to credit the team members who contributed to revisions through their insights and observations – that can’t help but build team spirit and a sense of ownership of the playbook.

To learn more, please visit: https://aventigroup.com/single-post/2018/10/11/unleashing-the-power-of-the-sales-playbook/

CSM & Product’ Is the New ‘Sales & Marketing’

By: Nick Mehta, CEO, Gainsight

If you take a look at my LinkedIn page (and scroll way, way down), you’ll see exactly where my career took a left turn. (No, not Chipshot.com—you scrolled too far!)

I started my professional career as a product manager.  Well, I tried to start my career by doing a Master’s in Computer Science in college, which taught me I wasn’t smart enough to be a developer, but maybe I could hang with them. Over the years, I moved up from Product Manager to “Manager of Product Management” (still a bizarre title to me!) and so on.

That was my career trajectory, and I couldn’t have been happier. It checked all the boxes for me—strategic thinking, working collaboratively, creativity, working with sales, and above all a total focus on giving the customer a great experience. Not to mention lots of PowerPoint!

When I left the world of product management to become a CEO, Customer Success was barely a gleam in my colleague Dan Steinman’s eye! But when I look back on it, I can see how it was preparing me for this crazy world of CS, and how the skills I honed in PM are so complementary to my job today.

For the last six years, we’ve been on a mission here at Gainsight to spread the word about Customer Success as the only way to drive sustainable growth in subscription businesses. Obviously, you can’t have a business without a product (and therefore a Product Management Team), and likewise, you can’t maintain a customer base without Customer Success.

The Customer Success Movement in 3 Acts

In the first act of our story, we tried to shine a light on the Customer Success Management (CSM) organization. We evangelized the value of a CSM team, we educated tens of thousands of people in the tricks of the trade, and built a worldwide network to help plug the right leaders into the right roles—all of which has led to CSM being recognized by LinkedIn as one of the top emerging professions in the U.S.

However, pretty soon it became clear: a lot of companies were building out a small, siloed CSM team to “own” Customer Success, but weren’t able to scale. We knew Customer Success needed to be bigger than any one team (as we say at Gainsight, CS > CSM). It’s a priority that needs to be woven into the fabric of the entire company—every department, every team. And the reason why is simple: to the customer, you’re all one company. The client doesn’t need to understand the differences between Sales and Support and Service and CSM and Marketing. Therefore your customer interactions need to be just as seamless. And so the second act of the Gainsight story was taking Customer Success out of that siloed CSM role and taking it across the company.

But as I spoke to people in the Customer Success community—as well as the CEOs of thousands of subscription businesses—I heard time and time again that one organization was missing from the conversation: Product. That resonated, because, as an ex-Product Manager, I saw how organically the two disciplines fit together. And in the “Age of the Customer” more than ever, most customers’ primary interaction with their vendors aren’t necessarily through their people, but rather through their products.

That’s why for our third act—simpatico to the third act of the Customer Success movement, we’re so fired up to announce that Gainsight has entered into a definitive agreement to acquire Aptrinsic, the first product-led growth platform. You can read more about the acquisition here.

Nick Mehta and Mickey AlonNick Mehta and Aptrinsic CEO Mickey Alon

The New Sales and Marketing

Here’s some conventional wisdom that’s at least as old as the mercantile system: if you want to achieve growth, invest in Sales and Marketing; acquire new customers. And in today’s economy, according to Gartner, 57 percent of the purchase decision is complete before a customer even calls a supplier. With that being the case, it was inevitable that Sales and Marketing platforms (think Salesforce and ExactTarget, Oracle and Eloqua, and so on) would come together to optimize growth through new customer acquisition.

It made a ton of sense. Sales teams wanted to understand prospect behavior, scale their engagements via marketing nurture, and influence marketing priorities. Marketing was interested in driving lead volume, learning from prospects, and iterating on campaigns quickly.

But in the Age of the Customer, CS teams have joined the ranks of Sales and Marketing in driving business growth by focusing on customer retention—more specifically, impact to net retention as a function of growth. However, for all of us who are building digital products and services, so many invaluable customer insights and personalized engagements are happening within the product itself. The analogy of Sales and Marketing alignment extends now to Customer Success and Product teams, who together are on the hook to deliver experiences and outcomes to both keep and grow customers.

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The same consolidation of Sales and Marketing platforms has yet to happen with Customer Success and Product technology—until now. We’re convinced that by partnering with Aptrinsic, we can usher in a new era of growth for subscription businesses with Customer Success and Product teams at its heart.

Gainsight’s New Capabilities

So what can you do with Gainsight and Aptrinsic? Our goal was to enable Customer Success and Product teams to work more closely together, as well as rally the rest of the company around the mission of driving Customer Success. In tandem, these two toolsets will give you the ability to fully leverage the product channel to generate even more powerful customer insights and actions. Here are just a few examples I would have loved back in my PM days:

  • Analyze the behavior of users in your product in terms of feature adoption, navigation, and retention.
  • Guide users to onboard and use new features through in-app engagements.
  • Solicit feedback from users in the product.

From both a CS and a PM perspective, we want you to be able to drive great outcomes and experiences whether inside or outside the product, whether delivered through automated digital outreach or human interactions (or a mix of both). And now, Gainsight is the only solution that enables companies to take full advantage of the shift to both digital and subscription, by providing Customer Success and Product teams everything they need to drive growth.

Where Can You Learn More?

To fill you in on all the details, I filmed a video with Aptrinsic CEO Mickey Alon and our very own Chief Operating Officer, Allison Pickens.

You can also learn more by checking out the following:


To learn more, visit: https://www.gainsight.com/blog/csm-product-is-the-new-sales-marketing/

Improve your Technology Marketing by Focusing on Business Outcome Messaging

By: Michelle Buckley

Developing messaging for professional services or software platforms often creates the “paradox of choice” for product marketers – the technical team or consultants explain they can “deliver anything the client wants” and with pride they list just short of about 5 million capabilities of skills and technology they have interacted with.  The paradox?  There are so many options, product marketers are not sure what choice to make.

The truth is that comprehensively describing in depth all possible product and service capabilities is the weakest way to generate interest from new prospects, and it’s not just because of “information overload.”  The reality is that technology buyer behavior has been changing dramatically over the last two years.  Business buyers drive the majority of IT purchases, even if funded out of IT.  As digital business becomes mainstream, CIOs are prioritizing business outcomes over technical service delivery.  As shown in the Gartner 2018 CIO Agenda research, CIO  priorities for 2018 focus on business metrics, from controlling costs and streamlining processes to driving revenue growth by exploiting data.

Furthermore, enterprise technology buyers tell us that the top reason technology provider campaigns inspired them to consider a solution (when they were not planning a purchase) was marketing messages that were “relevant to business issues, or triggered new thinking around them.”

For these and many other reasons, we are advising technology and service providers to lead their customer acquisition efforts with messaging focused on the business outcomes and value your offerings enable instead of the long list features, functions or capabilities available in your offerings.  Don’t worry, there will always be time later in the sales cycle to get technical.  But first, you need to inspire an opportunity with a hint of the business results that your offerings can deliver.

How can you refocus your technical messaging on business outcomes?  Start by researching the business outcomes of your own reference customers to capture insight. This can be done simply by interviewing reference customers, salespeople, or frontline customer service employees to learn what resonates with your ideal customers.  Sure they wanted new functionality, but what is the real reason they paid money for your solution (in one sentence or less)?  How did they justify the investment to their CFO?  This is the key to the customer insight that will inspire future projects and engagement in new logo customers.

To learn more, please visit: https://blogs.gartner.com/michele-buckley/2018/10/05/improve-your-technology-marketing-by-focusing-on-business-outcome-messaging/

How SaaS Broke Your Buyer Journey Map and How to Fix it

By Dennis Chepurnov

Most marketing and sales professionals are familiar with the concept of the buyer’s journey map. It’s a visual tool that helps align your organization’s marketing and sales tactics to the needs of your target buyers as they go through the process of selecting and purchasing a service or product.

Most buyer journey maps include the following six stages: identify need, determine solution, explore options, select vendor, justify internally and make purchase.

This model has worked adequately for many decades, but lately I find it lacking. This buying model has failed to keep up with changes in the market; specifically, the advent of software as a service (SaaS). Intended to transform how organizations deploy and pay for software, SaaS also has profoundly affected how customers go through the buying process.

SaaS Rocks

Buying enterprise software used to be an onerous undertaking that involved six to 10 months of requirements gathering, business case development, discovery, vendor evaluations and demos. It also entailed negotiations with IT and procurement and budgeting for the capital expenditures needed to acquire hundreds of thousands of dollars’ worth of required hardware and licenses. Several more months of deployment, customization, testing and training followed. During much of this process, customers had to commit key stakeholders to the buying process and deal with the resulting business disruption. Vendors also had to contribute considerable time and efforts from their account teams, professional services and training staff.

This still happens with large enterprise software deployments, but much of today’s business software buying has transitioned to SaaS and other subscription licensing models. This shift impacts both customers and vendors.

  • SaaS pricing and delivery make it easier for customers to invest in and—unfortunately for software vendors—divest from new software solutions.
  • The SaaS deployment model reduces the post-sale touch points with the vendor, for better or for worse.
  • SaaS has altered customer behaviors and expectations, even with non-SaaS products.

Although SaaS often costs more in the long run, buyers like it because it simplifies their lives. Vendors like SaaS because revenue is more predictable and often requires less involvement of professional services, which can be hard to estimate and staff.

The Vendor Trade-Off

It sounds great to have this perpetual subscription revenue, but there is a flip side: The buying process is never really over. With every subscription payment, customers have an opportunity to reflect on the value the software provides, then compare it to the cost they are paying.
The perpetual pricing model places the burden of ROI on the customer after the purchase; SaaS pricing effectively shifts it to the vendor.

This is a fundamental shift in the dynamics of value generation. With perpetual licensing, buyers staked their professional reputations—and sometimes their jobs—on significant investments of time and budget to acquire a technology solution. After the purchase, customers were responsible for ensuring the investment paid off.

With SaaS, a customer’s up-front investment is considerably lighter. Given the lower up-front investment of time and budget, the incentive to stick with a product is also lower. If a customer fails to see rapid value from your product, they are likely to move on to one of your competitors.

It’s often easier for customers to try a new product than to work with an existing vendor to ensure that the product works the way they need it to. I have witnessed many organizations sign on with a SaaS vendor only to drop them several months later and try another.

From the customer’s perspective, signing a SaaS contract doesn’t necessarily mean the end of the buying process. In fact (and this is where the floor drops away), while your sales team is ringing the gong and marketing celebrates another pipeline goal attainment, your customer may still be in an extended stage 3: exploring their options.

“It’s often easier for customers to try a new product than to work with an existing vendor to ensure that the product works the way they need it to.”


What This Means

Most marketing teams disengage from the customer’s journey at the point of purchase, just as the customer embarks on the most important stage of the whole experience: building business value from the product we sold them.

Buyers are our champions inside their organization. As a marketer, it feels somewhat disingenuous to abandon them just as they sign the contract. True, they may now be in the hands of other departments like account management, professional services and training, but those teams engage in tactical endeavors, and they often interact with different
customer stakeholders. But what about the decision makers we’ve catered to throughout the buying process? What happened to the strategic visions we painted for them? The industry insights we shared? Why should the story end here?

The customer’s journey does not end with the purchase, and we have SaaS to thank for making this painfully obvious. Marketers must extend the journey map beyond the purchase, continuing to support buyers as they derive business value from your product.

To that end, updated buyer journey maps should include a seventh stage: derive value.

Any organization that wants customers to succeed (and remain customers) needs to reassess the effort and focus they dedicate to this seventh stage. While many technology vendors promise to be their customers’ partner for success, few have actual programs to back it up, and fewer still engage product marketing—the authority on buyers and technology solutions— to help drive this effort.

Here are four thoughts to consider:

  1. Customer retention is not the refunds department. Sales and marketing professionals are acutely aware that it costs more to acquire a new customer than to keep an existing one, yet many organizations still view retention as a reactive measure used to salvage unhappy customers. Instead, customer retention should be a strategic marketing function to match demand-gen. Customer retention should work closely with product marketing, campaigns, sales and services groups to develop programs and touch points that actively help customers reach their business objectives and move forward.
  2. Don’t stop being strategic after your prospect becomes a customer. Many organizations shift to end-user marketing after the purchase (“here is our feature-of-the-week email campaign”). Facilitating end-user adoption is important, but not at the cost of ignoring decision-makers. After the go- live, your target buyers are still there, evaluating your product for success. Are you confident they will still believe they picked the right vendor when they pay your next invoice? It’s important to stay engaged in their efforts and continue to add value and inspire them. For example, developing and sharing a maturity model can help position your products alongside their long-term strategic business objectives and establish a framework for partnership going forward.
  3. Think of it as a buying cycle within the buying cycle. Many organizations “buy to try” SaaS solutions and look for rapid proof of value as an indicator of success. Think of it as an early proof of concept at stage 3. If your organization can proactively take on some of that burden of proof, you stand a better chance of turning stage 3 into stage 7.
  4. Celebrate the contract. It’s a big deal to sign a paying customer, and a lot of people work hard to make it happen. But for customers, the purchase is just the beginning, and your team should view it as a milestone for your marketing strategy, not the end goal.

We live in an era of seemingly endless options. Consider how many times you have downloaded a new app on your phone, tried it for a few minutes and then promptly uninstalled it when you realized it did not meet your needs. Today’s B2B buyers have a similar mindset. If you fail to help buyers actualize the value of your product after purchase, it won’t take them long to start looking at the next vendor.

To learn more, visit: https://pragmaticmarketing.com/resources/articles/how-saas-broke-your-buyer-journey-map-and-how-to-fix-it?utm_source=PMC+1809+&utm_medium=Newsletter&utm_content=Article&utm_campaign=Partner+influencers