Studies In Selling: One On One With Craig Rosenberg

I spoke to Craig Rosenberg, co-founder of TOPO, about his best sales advice

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Adam: Thanks again for taking the time to share your best sales advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?

Craig: I’m the chief analyst and co-founder of TOPO, a research and advisory firm that helps sales and marketing organizations adopt the patterns and plays used by the world’s fastest-growing companies. I have 20+ years of sales and marketing experience with TOPO’s dataset to provide specific, actionable recommendations that help companies drive predictable, scalable growth. TOPO supports 240 companies, from the world’s largest technology companies to startups.

Before founding TOPO, I built expertise across the funnel, from marketing to sales. I spent years consulting, building sales development and sales processes, and more years as VP of Marketing for a business media company.

Adam: What is the single biggest sales mistake you have ever made and what did you learn from it?

Craig: I don’t have any catastrophic sales stories—which is a bummer because those are fun. I’ve been consistent. I make mistakes 60% of the time and nail it 40% of the time.

In my early days at a startup (Series A), we closed the biggest deal in company history with a Seattle startup. Months later, they got exposed for “cooking the books”; they were gone within 24 hours. The lesson is not “Avoid companies that can’t pay.” It’s “Question everything.” We were too excited to wonder; how can this company outspend the biggest tech companies in the world?

So be skeptical and ask questions, and you’ll find the holes to plug to win more deals.

A recent example from my customers illustrates this, the VP of Sales reviewed a deal with a sales rep who was bullish on an opportunity. The VP suspected that the customer lacked a compelling reason to buy. The rep said, “Who cares? It’s a deal we can close this quarter!” They set up a conference call and discovered that the champion, in fact, couldn’t justify buying. The sales team collaborated with the prospect to build a better use case, and they won the deal.

Skepticism made the difference between winning and losing.

Adam: In your experience, what are the key pitfalls to succeeding in sales and how can you overcome them?

Craig: Two pitfalls go hand in hand: the inability to listen and the inability to convert what we learn into compelling action.

Every sales methodology has a listening component. It’s simple: via questions and messaging, sales must understand a buyer’s situation and objectives. Sales can then customize its messaging to resonate with the buyer. Even the “sell me this pen” exercise (made famous in The Wolf of Wall Street) is a listening exercise. When I ask you to sell me this pen, you don’t pitch the pen; you say, “Happy to. First, I have to ask, what interests you about this pen?” or “I read that you are a Director of Logistics, can you tell me more about your role and how you are measured?”

Which leads us to the second pitfall…

Many organizations arm sales with questions to ask and techniques to use. They don’t help translate this guidance into customized messaging. We listen to hundreds of sales calls per year. Too often, while the listening portion goes well, the follow-up messaging is a disaster. What’s the point of asking questions if you just give the same pitch to everyone?

The solution lies in training and real-time enablement. First, provide messaging that connects with common answers to the questions. Follow this up with exercises in which sales asks a few questions and immediately turns the answers into relevant messaging. Alternatively, we can look to technology and provide a platform, enabling sales people to get needed answers. Example: combine the real-time collaboration of Slack or Microsoft Teams with an application like Guru, which can turn the answers to questions into a real-time wiki for future reference.

Adam: What are your three best tips when it comes to selling?

Craig: Let’s focus on tips for managing meetings and often neglected set of skills:

  1. Start each call by stating its purpose, the agenda, and the desired outcome.
  2. Close the meeting by identifying next steps and putting the next meeting on the calendar.
  3. Within 24 hours, send an email that summarizes the meeting and documents next steps.

Adam: Describe your sales methodology. Have you found that different types of prospects are responsive to different to types of styles, and if so, do you adapt your style to the type customer you are selling to?Craig: Sales comes down to six plays: prospecting, discovery, pitch/preso, demo, trial, and proposal. Most sales processes contain these core elements.

Our design principles:

  1. Play design depends on the target market. A demo to an enterprise company is a highly custom, F2F exercise, while an SMB demo is virtual, templatized, and compact.
  2. Play design must reflect the needs of each stakeholder. Don’t give a two-hour user demo to an executive.
  3. Each play includes audibles that address the needs of a unique buying process. If the prospect wants an overview of the market for their team before they talk about product, then enable to be able to do that. The buyer won’t necessarily follow your desired path.
  4. You win or lose sales at the beginning of the process. Discovery is critical.

Adam: What sets your approach apart from others in your industry? Describe your industry and your best tips specific to selling within it.Craig: We are not beholden to any legacy methodology. We continually study the best sales organizations to learn what it takes to win today.

For example, we recently created a new demo approach: IDD (insight, discovery, demo) because organizations were seeing low post-demo conversion rates. Where product demos are often one-way presentations of features and functions, IDD calls for the demo to comprise a few “chapters” or product areas that you want to demonstrate. Each chapter is its own micro-demonstration and starts with an insight (“Our research of your peers indicates that…”), includes discovery (“What is your approach to…”), and ends with an engaging demo of the solution that is tailored to the buyer’s needs.

Adam: What do you believe is the hardest step in the sales process and how can it best be navigated?

Craig: Prospecting, or getting people’s attention. Today’s buyers are distracted: inundated with emails, no desk phones, no time to speak with you anyway. Every salesperson must do this:

  1. Use a multichannel, multitouch approach to buyers. A 2-3 week campaign of 8-12 touches combining email, phone, social, direct mail, video, and more.
  2. Customize. Relevance is the only way to stand above the noise. Craft messages that resonate with buyers. This may mean that you don’t directly pitch your product.

Adam: What are your best tips for improving your close rate?

Craig: Deals are won early in the process. Here’s how successful reps work on winnable accounts and opportunities:

  • Use deep discovery to understand the buyer’s situation.
  • Create a solution that delivers a better future for the buyers.
  • Leave no stone unturned in managing the buying process.

Organizations often think they need “negotiation tactics.” In fact, they’re working on bad deals that weren’t managed and for which no value was created.

Sales reps who manage the front end of the sales process don’t discount.

For specific tools for the end of the sales process, the close plan improves close rates. It’s an agreement between sales rep and prospect listing the milestones that each must complete to close the deal and deploy the solution. It captures the agreed-upon next steps with dates working backwards from deal signing or implementation. By assigning accountability and ownership to all stakeholders involved and creating a mutual commitment to move toward a deal, you enable all to anticipate misunderstandings and challenges.

Adam: What is your best advice around making the ask?

Craig: Make sure that the buyer sees value before you ask for anything.

The other thing is, you must ask! Sounds simple, but sales reps often hesitate to just ask the question.

Adam: Language is obviously important throughout the sales process. What are key phrases or words you have found have helped or hurt your chances of success?

Craig: Here’s what tells the buyer that I’m listening and committed to understanding. “Got it. Let me see if I can play this back to you.” You won’t always get it right, but once you put what you’ve heard in your own words, the buyer can fill in the gaps.

Adam: On a scale of 1-10, how important are ethics to succeeding in sales? Explain.

Craig: 10. Sales is about trusted relationships, and ethics is a core element of trust. In our markets (B2B tech and SaaS), differentiation—from feature parity to commoditized messaging—is increasingly difficult. To an increasing extent, differentiation comes from the relationship and experience a buyer has with sales and the organization. Even when the news is bad, the buyer respects you when you tell the truth.

A buyer once told me that she judged sales reps by their ability to tell her what they can’t do.

Adam: What is your best advice on how to best manage and stay on top of leads?

Craig: Organizations must operate a team of phone/digital-based sales development reps (SDRs) that identifies, connects with, and qualifies leads. The SDRs then pass the qualified lead to a salesperson who takes over the sales process. As a result, leads do not go untouched. The team is dedicated to follow-up, so the requisite amount of effort (multiple touches) is applied. The evidence is in the numbers—the SDRs enable an exponential increase in conversion rates.

Adam: What is the single best piece of sales advice you’ve ever received?

Craig: “People don’t buy Legos. They buy the ability to build the Millennium Falcon.” I heard this from Stephanie Buscemi, now the CMO of I had asked her to identify the biggest thing she had learned while at Brio. When they moved from selling features to selling use cases and solutions, they saw explosive growth.

Adam: What sale are you proudest of? Walk through how you made it happen and its significance.

Craig: My twin six-year-olds sold $5K worth of popcorn (at $25 per bag!) for the Cub Scouts. They were the only kindergarteners to make “quota.”

I learned a lot!

  1. It’s a numbers game. For every three people that got the “Would you like to buy popcorn to support us?” pitch, one said yes. They kept pitching.
  2. Target the right people. The kids set up in front of a high-end grocery store.
  3. Ask! Simple. They were not afraid to ask for the sales.
  4. People buy from people they like. Most people bought because the kids were “so cute.”

Adam: What is one thing everyone can do today to become better at selling?


  1. Outline all the steps, from prospecting to close, in your sales process.
  2. Document what happens in each step and what is required to move to the next one.
  3. Commit to solving one step at a time (every 1-2 weeks).
    For example: week 1: prospecting. week 3: pitch. week 4: demo
  4. Re-evaluate everything (record your calls).
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