PODCAST 86: Strategic Vs Tactical Approach in Sales Planning with Mary Rogul

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This week on the Sales Hacker podcast, we speak with Mary Rogul, a VP Sales Consultant, who’s currently an Enterprise Sales Advisor at Crayon.

Fresh out of college, Mary started out in accounting, but it didn’t take long before she began a 20-year sales career that led her through Monster.com, HubSpot, and several others. She’s now a consultant helping VPs of Sales scale and build their sales teams.

If you missed episode 85, check it out here: PODCAST 85: AI will not replace SDRs/BDRs w/ Dan O’Connell

What You’ll Learn

  • Who is Mary Rogul
  • Motivations of an individual contributor vs. a manager
  • How great sellers approach their day

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Show Agenda and Timestamps

  1. Show Introduction [0:09]
  2. About Mary Rogul and Crayon [2:14]
  3. Mary’s journey into sales [5:14]
  4. Mary’s sales method: dive deep into the customer [7:52]
  5. If you’re not prospecting, you’re losing money [9:55]
  6. Common mistakes Mary sees other sales people making [12:29]
  7. Advice to young salespeople: Try. Explore. Discover [22:05]
  8. Strategy is setting goals, tactics are the outline [25:12]
  9. Heart is what ultimately makes a great seller [29:48]
  10. Sam’s Corner [33:20]

Show Introduction

Sam Jacobs: Welcome to the Sales Hacker Podcast. We’re excited today to have on the show Mary Rogul. Mary was most recently VP of Sales Strategy and Engagement at Crayon, where she’s now an advisor. She’s also been a high-performing individual contributor — she was part of the team that drove a lot of growth at HubSpot as it went from small to large, and she worked under Mark Roberge. If you’re an individual contributor out there and you’re wondering about this path to success without having to run and lead a huge team, I think this will be an interesting listen for you.

Now before we get there, we want to thank our sponsors. Now before we get there, we want to thank our sponsors. One of them’s brand new. It’s a company that everybody’s heard about — DocuSign. Every sales org feels the pressure to close deals faster. Take control with the DocuSign agreement cloud, a suite of tools that automates sales contracts and quotes ,all right in your CRM. Create custom contracts in a click, sign them digitally, and automatically pull data back into your opportunities. See why more than half a million businesses use DocuSign with a free trial and discount exclusively for Sales Hacker listeners at go.docusign.com/saleshacker.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Mary Rogul.

About Mary Rogul and Crayon

Sam Jacobs: Welcome to the Sales Hacker Podcast. On the show today we’re incredibly excited to have Mary Rogul. Mary is one of the leaders in the go-to-market and sales space and sales community in the Boston area. Most recently she worked at Crayon, which is an early-stage market intelligence platform. She’s now an advisor to Crayon and is also working with a number of other high-growth companies. She worked at HubSpot from 2009 to 2015 and was part of the enterprise scale up from 2011 through the IPO in 2014. She’s also a frequent speaker and panelist for the Women in Sales Leadership and Women in Tech communities; and was recently voted one of the top 20 women to watch by SMLA. Mary, welcome to the show.

Mary Rogul: Thank you. Very happy to be here.

Sam Jacobs: We’d like to start with your baseball card.

Mary Rogul: So for Crayon — I ended up as a full-time leader of sales because I was advising to them. After HubSpot I realized I like doing a bit of everything — product, customer success, etc. I wanted to understand how we could all collaborate and play well together, and that landed me with some of the folks over at Crayon.

I’ve been at Crayon for about a year, and we were able to grow that team from about 10 folks when I joined to 22 when I left. They’re doing fantastic — penetrating not only the Boston and New England market, but we’re really seeing them make some serious strides nationally.

Sam Jacobs: What does Crayon do?

Mary Rogul: Crayon is a market intelligence competitive platform, and they allow their customers to have a good pulse on what their competitors are doing ahead of time so they can make good decisions on competitive advantages.

Mary’s journey into sales

Sam Jacobs: How did you get into sales? Walk us through a little bit of that background.

Mary Rogul: I actually graduated college with an accounting degree. I did that for 5 or 6 years and was done with it. I went into a staffing firm — I think it was Hollister Associates — here in Boston. I walked into their bullpen of sales folks, which was a bunch of headhunters, and I heard the buzz on the floor, and I thought to myself, “I want to do this. I can do this. I understand accounting and finance. I can place accounting and finance professionals.” That’s how I got into sales. So, I was a headhunter for about 7 years, and then I was recruited over to Monster.com. My intern at Monster had gone over to a very not-so-well-known small startup in Cambridge, when they were about 80, 85 employees and recruited me over to what is now known as HubSpot. So that’s how I got into software.

Sam Jacobs: At HubSpot, were you an individual contributor or did you run teams?

Mary Rogul: The majority of my contribution in sales has been as an individual contributor, and that’s by design, because I love being in the trenches with the customer. So my entire tenure at HubSpot was as an individual contributor, although I did some team-leading exercises. I always chose to stay there at the forefront, and then often in my career I would get recruited into a sales leadership or management role, and then I would find myself just going back and forth, always drawn back into that individual contributor role.

Sam Jacobs: What is it that you love so much about being an IC?

Mary Rogul: I love driving the deal. I love building the relationships. I like to be involved with the customer’s business. I like to understand the inner workings, be the center of the collaboration. I love the quarterback focus, where I can be strategic internally and help resources really come together to do what’s in the best interest of the customer, and I love helping the customer figure out how they can do things differently.

Mary’s sales method: dive deep into the customer

Sam Jacobs: Do you embrace any kind of sales methodology? Walk us through your process as a top-performing IC.

Mary Rogul: I don’t know if I would say it’s a specific process, but I do have my own steps. I always start with what I reference as an intake. I start everything with learning. I go into the databases, I look at Salesforce, I look at all the notes, I work with the existing account executives, and I get very, very familiar with what’s happening. Then I start the conversations, and I start to weave together a story. I approach it from, “How can I help? How can I help this account get more from the platform, get more from the tool suite? What are the gaps, what are the obstacles, what can we do differently to make sure that they’re getting the majority of what they need from this platform for the investment they’ve made?”

If you’re not prospecting, you’re losing money

Sam Jacobs: Do you block off time to prospect?

Mary Rogul: If I’m not prospecting, I’m never going to hit my numbers. I don’t necessarily do it on my calendar, which I recommend doing if you’re not disciplined . 7:30 to 9:00 in the morning are prospecting hours, along with 5:00 to 7:00, or even on the weekends a bit. Blocking off times at the beginning and end of the day is crucial for prospecting. If I’m not on the phone during my work day, I’m not making money, and I’m not doing what’s in the best interest of my company. Prospecting is key, but you must balance it with the deals coming in.

Common mistakes Mary sees other sales people making

Sam Jacobs: What are the common mistakes you see salespeople make early in their careers?

Mary Rogul: The thing I see most consistently is, once you get someone that has an interest, the rep gets into pitching right away without being inquisitive, without asking questions and getting into a conversation to learn and understand the prospect’s environment. You must understand what you’re talking through before you start talking about why your product or your tool suite is so great and how it’s going to solve all of their problems.

Number two: Lack of followup. After someone has a conversation, they’re not sending an email that says, “Hey John, based on these 3 things we talked about this morning, it sounds like there could be a reason to move forward into a demonstration. What I heard is this. Let me know if I’ve not heard this correctly, but I do feel like there’s a reason for us to spend some time together.” That type of followup keeps the deal moving, and it has to be done in preparation. It has to be done after a phone call, and it has to be done to dictate any type of demonstration or executive conversations. I don’t see it happening.

Advice to young salespeople: Try. Explore. Discover

Sam Jacobs: There’s a lot of pressure for high-performing sales people to move into management and leadership. Is there a way to help a young person figure out, are they equipped to be a great leader or manager, versus pursuing an individual contributor track?

Mary Rogul: The best way to figure that out is by doing as much with the customer as you can and figuring out what you love about that. Also, just by evolving within an organization, you’re going to cross paths with folks in and outside of sales, and you figure out where you belong because of where you sit within the organization and where you gravitate.

My recommendation to young folks in the early years of their sales career is to drive as many deals as you can as an individual contributor. Because that in and of itself is incredibly valuable. You are bringing success and revenue to your company and to your customer, and that will really pave the path for your career, and then you can do whatever you want to do. I think it’s a very hard thing to figure out when you’re younger. You have to experience different positions, different roles, and different people, and then you will evolve over time to what you love to do.

Strategy is setting goals, tactics are the outline

Sam Jacobs: You’ve commented in the past about the differences between a strategic approach and a tactical approach to revenue generation. Walk us through the differences between those 2 approaches, and why it matters.

Mary Rogul: I’m always wanting to advise tactically, but it’s extremely time-consuming, so I can’t take on as many clients. I’ve been advised and mentored to take a more strategic approach.

Strategic planning lays out the long term, the broad goals that a business or an individual wants to achieve; the tactical piece is the outline. If I run into a team, for example, that’s consistently struggling to hit a monthly sales quota, it’s likely time to reevaluate some of the tactics the sales reps are using to prospect or to close. Or, the quota strategy might need to be shifted depending on how badly they’re missing the mark.

I look at a sales plan to encompass both strategic and tactical planning. I include these components in a strategic plan, and one is the background of the company or of the business:

  • What’s happening currently in the environment?
  • Where do they stand?
  • Where do they want to be in the future?
  • What do they want to accomplish in the near term?
  • What are their goals?
  • Who’s responsible for these goals?

So that’s how I map that out.

Then I have a tactical plan that outlines how they achieve this final result.

Sam Jacobs: What typical actions are you measuring or evaluating?

Mary Rogul: Number one: We must fill the pipeline with more leads, right? Whether that’s in the next week, the next month, whatever that looks like. So how do we do that? Do we spend an hour a day prospecting? Do we go into our social networks? Do we join different LinkedIn groups? Do we attend networking events? So number one, fill the pipeline.

Number two: We want to close more deals each month. So do we get reps involved in training sessions for different product offerings? Do we set a goal for each rep to schedule at least 3 to 5 demos a week with their prospects? That’s number 2, closing more deals.

Number three: Do we hire more sales reps by the end of a particular quarter so that we can create that hiring profile, develop outreach campaigns to find and attract talent, attend career fairs, etc.?

Heart is what ultimately makes a great seller

Sam Jacobs: When you look at the qualities that make a great seller, what do you think they are?

Mary Rogul: I would say first and foremost is heart. Someone has to be really excited to sell what they’re selling. A lot of people think sales folks are just driven by money, and it’s more than that. Some level of money motivation has to be there, but you can’t sell something you don’t care about.

Sam’s Corner

Sam Jacobs: That conversation with Mary was truly insightful, specifically the piece about how great sellers approach their day: how they block off time for prospecting, listen to the customer, focus on having high-quality conversations, use empathy to deliver results, and, frankly, how some are more motivated by being an individual contributor, and some are motivated by being a manager. Sometimes the role and the skills and requirements of executive leadership present themselves just because you’re so talented and so capable, that organizations need you at a leadership level. But, there are also thrills and joys of just being involved in a customer conversation and helping customers solve problems. Lastly, I loved the stuff of why we got into sales, and why we find passion and joy from sales.

What We Learned

  • Who is Mary Rogul
  • Motivations of an individual contributor vs. a manager
  • How great sellers approach their day

Don’t miss episode 87 (next week’s episode)

I hope you enjoyed the show. Before we go, let’s thank our sponsors.The first is DocuSign. Execute contracts and get to revenue faster with DocuSign, used by employees in 90% of the Fortune 500 businesses. Learn more at go.docusign.com/saleshacker. Our second sponsor is Outreach, the leading sales engagement platform

If you want to reach out to me with feedback, you can reach me on LinkedIn. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

This is a sponsored guest post from a Sales Hacker partner.

Sam Jacobs is the Founder of Aqueduct Revenue Advisors and the New York Revenue Collective and regarded as one of the top start-up CROs in the tech community.

He has has over 15 years of experience scaling companies from post-revenue to ~$300M, has helped raise over $400M in institutional capital, and has helped companies of all sizes achieve an average annualized revenue growth rate of 48% over the last 15 years.