Sales Enablement PRO Podcast Sales Enablement PRO

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Debbi Varela, the author of Put Me In, Coach, here with us today. Debbi, I would love for you to introduce yourself, your role, and your organization to our audience. 

Debbi Varela: Absolutely. Thanks for having me. My name is Debbi Varela. I have over 15 years of experience now in the sales enablement and transformation space before it was even really like what it is today. I have been lucky enough to have worked with some of the world’s smallest startups to some of the world’s largest tech companies. After working in these businesses of all sizes throughout my career, I have honestly met some of the coolest and most interesting people. I’ve learned so much about what works, what doesn’t work, why it didn’t work, and what to do next time. 

SS: We’re excited to have you here, Debbi. Now, going back to your book, you actually discuss how coaching can create a culture of success for businesses. In your opinion, what are the key components of a successful sales culture?

DV: That is a great question. Funny enough, I actually had just published a blog on my website on this exact topic a few weeks ago. I believe the recipe to create a winning sales culture is really around five key things. The first one for me is really just having a defined vision so everyone understands what their position is on the field or where they fit into the bigger picture of the organization. I just feel this is incredibly important because it gives a sense of belonging and purpose to individuals.

The second one I think it’s a key element that I’m passionate about, which is really around skill, or sometimes I call it action mapping and motivation. What I mean by this is truly knowing your team member’s strengths and their areas of improvement and how to motivate each person. Where will they naturally excel? Where will they need a little bit more encouragement? What’s the best way to encourage them? Are they extrinsically motivated or intrinsically motivated? That makes a huge difference. 

The third one I think is super important, which I see time and time again in organizations, is accountability and continuous feedback. That would honestly come in as one of the most important ingredients for a thriving sales culture. Interestingly enough, with many of the companies I’ve worked with, this is oftentimes their biggest weakness. When I say accountability, I’m talking about like, do you manage behavior? Do you as a leader take responsibility or do you blame other people? Do you manage your pipeline and then do you spend enough time on pipeline reviews? Do you have a cadence that you’re holding yourself and your team accountable to? That’s what I think of when I think about accountability.

The next one is really around team building and trust to ensure that your team operates as a single unit. You can see this really play out on the sports team when teammates trust each other and they really know each other. Things just look effortless for them and they just flow together.

Finally, for me, it’s the last one on my list, but it’s honestly just as important, which is celebrating successes and learning from failures. You should celebrate every win, no matter how small it is, because it’s still a win. I feel that setbacks should be reviewed with positive intent, not to blame, but to learn any ball from those.

 SS: I love that approach. Especially today in the current environment, why is coaching critical in today’s sales environment and how does it help nurture a healthy sales culture?

DV: I think coaching is absolutely critical and honestly it’s interesting because I think that most people wo

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Andy Springer, the chief client officer at RAIN Group, join us. Andy, I would love for you to introduce yourself, and your role in your organization to our audience.

Andy Springer: Hi, everyone. Thank you very much for having me. I am Andy Springer, the Chief Client Officer at the RAIN Group. My role is one that each and every day I am a practitioner leading teams in terms of supporting large-scale sales transformations and also working with small, and medium-sized enterprises in terms of upscaling and developing sales skills that are going to shift the dial in terms of sales performance.

SS: Wonderful. The reason that we wanted to pull you on to this podcast is because RAIN Group actually recently released a study that identified some key trends in the current sales landscape. In your opinion, what are the trends that have the greatest impact on businesses and their ability to succeed in the current environment?

AS: Yeah, I would say that the trends that we saw through our research were a significant increase in terms of sales cycles. Opportunities are taking longer to close. There’s more complexity in terms of that. The amount of opportunities that are being led to a loss due to no decision. While there may be significant needs, significant problems to solve, and objectives to be supported to achieve, for whatever reason we’re seeing a lot of no decision being what they lost to instead of competitors.

I think the third one is selling in an uncertain economy. If you look at the post-pandemic world and you look at the political challenges that have impacted the market, you look at the shift in terms of the financial impacts in terms of the post-pandemic inflationary world and then how that’s changed the dynamics of the economy, it’s made it really challenging particularly in the B2B space, but not exclusive to. That uncertainty cascades uncertainty in terms of sellers and how they approach the market and what they are dealing with.

SS: Absolutely. I couldn’t agree more. From your perspective, Andy, how have these trends influenced or created top challenges that sales organizations are facing today? What would you say those top challenges are?

AS: I think it was pretty clear from our research that in terms of when I look at it through the lens of a sales leader and sales enablement space, one of the most consistent challenges that keeps showing its face in the sales space is recruiting and hiring sales talent and the associated challenges with that.

Also, the uncertain economy piece was represented very strongly, generating qualified sales leads continues to be a significant challenge for a lot of organizations. We dive into the skill areas where the key challenges in developing sales skills are relevant in the real-time selling environment. Also, the one which I found unsurprising, but I think some who I’ve spoken to in reflection on the report found surprising, which was the challenge of developing sales managers. Often in the sales enablement space, I see that sales managers are the ones who are most forgotten about. They’re also the ones that are often the loudest in asking, requesting, and demanding skills from their sellers. Often when it comes to developing skills for them to be better managers, it’s something that they’re either left out on, it’s not a focus or it may not be that there’s a budget to focus on developing them.

SS: Absolutely. Yeah. I couldn’t agree more. To that point, especially for our audience, what role can enablement play in helping businesses overcome these challenges?

AS: I think there are three key areas that we’ve really isolated and focused on.

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Jay Shephard at Bentley Systems join us. Jay, I would love for you to introduce yourself, your role, and your organization to our audience.

Jay Shephard: Thanks for the invite. I’m thrilled to meet you and spend some time with you. Where do you start? I have been doing this for a while. I started my career 25 years ago selling, and when you start your career in selling you start to pick up some things that seem to go well. All of a sudden I started being asked to do some coaching with new hires that were coming in by my boss. What I found out, Shawnna, is I loved it. It’s a lot of fun.

I thought, is there a career around this? I love selling, but I also love the coaching element. That’s how I kind of, we’ll call it backdoored into this thing called enablement. Specific to enablement, it is an evolving picture, which I’m sure we’ll get a chance to talk a little bit more about.

I’ve had an opportunity to work primarily in the enterprise software space in both sales effectiveness tools as well as software platforms. I started with Bentley in 2023 and really took on a very cool challenge and that was to redesign, revamp, and repurpose enablement to be more of a strategic aligned value add to our CRO. That’s where I am today.

SS: We’re excited to have you here, Jay. Now, a key focus for you at Bentley Systems is really, as you’ve stated in your intro, reframing the way that your organization thinks about enablement. From your perspective, what are some of enablement’s core responsibilities and what is the value that it brings to the business?

JS: I think enablement, the industry, the space, whether it’s in the United States, Europe, or Asia, doesn’t matter, it is in flux. In other words, if you ask 15 people what the definition of enablement is, you can get 25 answers. When it came to coming to Bentley, what we figured out early on was the fact that there is this talented group of people that make up the enablement team, but they were misunderstood. They were almost pushed into a corner and almost like enablement became the department of broken things, as I always call it.

They were an afterthought. It was the last thought, like oh yeah, we better get enablement involved. Well, that’s really not the purpose of enablement, but it was created to be that way based on just general culture and a lack of definition of the value of what enablement brings.

SS: Jay, I know that you created a sales enablement charter, which really kind of focuses on outlining the mission, the goals, the strategy, and the responsibilities of your enablement function. Tell our audience more about this. What are your best practices for creating an effective enablement charter?

JS: I’ll start off by saying the reason I went to Bentley. It had everything to do with the CRO. He wanted to lead a transformation project, initiative if you would, company-wide to drive the strategic value of Bentley Solutions to their end customer. The CRO realized that there were some significant gaps in there, which of course was enablement.

I took this position first and foremost because it was aligned with the CRO. I think that’s really important for your listeners to know. The CRO is critical to the direction, as well as the strategic value of what enablement brings. Knowing that, connecting with our CRO as I did through that interview process, I knew this was an opportunity I wanted to take advantage of.

Knowing that we were going to start from scratch, we went out and essentially asked individuals who were key to the business all throughout the globe, 1, what is your definition of enablement? You would not believe how man

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Rodney Umrah from Forcepoint join us. Rodney, I would love for you to introduce yourself, your role, and your organization to our audience.

Rodney Umrah: Thank you so much, Shawnna. I am delighted to be here. My name is Rodney Umrah, and I’m the global head of enablement at our go-to-market organization here at Forcepoint.

SS: I’m excited to have you here. Now, I know that you’ve shared that enablement found you rather than you finding it. Tell us a little bit about that career journey. Why and how did you transition into the enablement field?

RU: I’ll take you back a little before I get to the transition because that will help to inform why that experience was so interesting to me. I was born on the lovely island of Jamaica, Shawnna. I’m not sure if you have been there before, but that’s where I was born. I went to the University of the West Indies and I studied computer science. I was fortunate to be hired right out of school by IBM. There’s a gentleman who did that, and I don’t know how I can pay it forward to him, his name is Carl Foster. He’s still my mentor and friend today. He saw something in me that I didn’t see in myself.

While being at IBM, there were 366,000 people in the organization. That was the largest IT company at the time, but it was like a university really, and I learned a lot. That’s where my true professionalism was honed. I migrated to Canada, that’s where I live now, and I was in technical roles between IBM Jamaica and IBM Canada, but I always wanted to be in sales. I transitioned from technical roles at IBM to sales, specifically software sales.

Now, a little bit of context, Shawnna, is that my mother is actually a teacher and my brother is a professor. I used to do that part-time, I was a part-time professor myself, so, as a result of that experience, enjoying the IBM experience, and doing well, I said I wanted to transition to Microsoft. I spent about eight and a half years at IBM, then over to Microsoft. I was there for five and a half years and then moved over to NetSuite. This is where, now, your question comes in, Shawnna, which is a transition. I was doing well in sales at NetSuite, going to club every year and especially leveraging my manager at the time. He was very instrumental in my success.

My GVP or Global Vice President of Sales, invited me into his office one day, and just asked me the question: are you interested in leading enablement? Now, the truth is I didn’t know what that term meant, enablement. I was like, enable what? I didn’t know because I was used to the term training. He asked me to speak to the leader of that organization because the GVP wanted me to lead enablement for his organization. As a result of that, the rest is history as they say, because here I am 10 years later and really, really enjoying it. I’ve been all over the globe, Shawnna. I was in Australia, the Philippines, Europe, across the US, Canada, you name it. I just have a great passion for the enablement vocation.

SS: I love that career journey, and I’d love to understand more about how you think that your non-linear career path and your background in roles, spanning sales and academia, have helped you in your role as an enablement leader.

RU: It certainly did, especially because I came from a sales background. It was, as I said, my group vice president who saw it in myself and also my manager. At the time, my manager asked me to do some best practices training with the team that we had at the time and it kind of grew and so they saw it and I didn’t.

As a result of having the sales background and then being able to enable sellers, there is instant cred

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Regan Barker from Grant Thornton, Australia join us. Regan, I’d love for you to introduce yourself, your role, and your organization to our audience. 

Regan Barker: Absolutely, Shawnna. It’s great to be here. My name is Regan Barker and I am the head of sales and sales enablement here at Grant Thornton Australia. Part of my role is to work closely with the business on their sales activity and sales coaching. Grant Thornton is an accounting audit and consulting firm. We have six offices across our beautiful nation and seven service lines. We sell over a hundred products and services across 11 industry specializations with about 170 partners and 1,300 people. 

SS: Thank you for joining us. We’re excited to have a guest on the podcast from the Australia region. Now, one area of expertise for you is coaching. I’d love to start there and understand why sales coaching is so important. 

RB: Great question. I think for particularly working in professional services, slightly different from more product-based businesses, our partners are the owners of the business. They’re also the experts and they’re actually the product. For me, coaching and advising our 170-odd partners is pivotal. 

In Australia, we have an ever-changing landscape across the business, regulation, and market pressure. We need to ensure that our partners and our people have the confidence to cut through the noise and really provide essential insights around business operations, regulatory change, and emerging issues for those businesses and senior leaders to make sound business decisions. Helping our partners in their activity helps them be more efficient as well as to be able to make sure that they’re talking to the right people around the right insights as well.

SS: Absolutely. From your perspective, what are some of the key components of an effective coaching program, especially in today’s sales landscape? 

RB: I think for effective coaching, it’s really about meeting people where they are. Most sales programs are based on supporting sales operators, our partners are the owners, and service providers, they’re the team leaders. They have to run the billing, run the client programs, absolutely everything. Our effective coaching has to be integrated as a part of their everyday life to make sure that it is effective and efficient. 

When I say meeting people where they are, really it’s about understanding their business, how it operates, what the sales cycles are, whether it’s heavily compliance-driven and you’ll be advising an organization and their CFO, for example, on a regular basis or cyclical basis versus some of our financial advisory experts that are heavily transactional. Meeting them where they are, both in how they operate, but also in terms of their own capability as well, some of which are extremely effective sales operators and others may be more introverted. It’s really about giving them confidence.

One of the pieces that we try to focus on is just focusing on one skill or development area at a time. Fine-tune that, making sure we find our efficiencies, and then as they build that confidence and capability, then we move on to the next area to help fine-tune something else, another skill. 

SS: I think those are absolutely key components to effective coaching programs. In your experience, what does good coaching look like? In other words, what does it take to be an effective sales coach? 

RB: I think the most powerful tool you can have is to also be a practitioner. In professional services, obviously, I’m not going to be a tax expert, I’m not going to be an auditor, but what I am is an

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Marja Moore join us. I would love for you to introduce yourself to our audience.

Marja Moore: Thank you, Shawnna. Hi, everyone, my name is Marja Moore, and I am in the Seattle area. I have most recently worked at companies like SAP, Concur, and Infoblox. Right now, I’m taking some time off to explore some new adventures, but I have worked in everything from marketing to business development to sales enablement and value methodology building. I have a diverse background in many industries and I use all of that to inform how I go forward with every new role, especially with enablement. 

SS: Wonderful. I’m excited to chat with you. There was something on your LinkedIn profile that caught my eye. You mentioned that you lean toward being a human-centric leader who is also focused on data-driven outcomes. I’d love to understand from you, why are both sides of this coin important as an enablement leader. 

MM: I would say it’s an important thing to have for any leader. First of all, we’re dealing with humans every day. You need to know what’s going to compel people. What’s going to get them to do what you need them to do, not only perform in their roles but also in the organization? How are they expanding their view? How are they becoming greater than what they were before? Understanding who you’re working with, whether that be people on your team or people that you’re trying to enable, you need to understand their values and what makes them tick is important.

I think every enablement leader will say, you always have to give them what’s in it for me. I think this is true for literally any leader you need in order to compel somebody, you’re going to need to know who the human is behind it. That’s important to me, not only knowing the people that I help lead, but those that I help enable. What are their needs? What compels them? What gets them to do the things that we need them to do, and how does that make them feel? 

On the other side of the coin is the data, and that is really driven by the need to say, okay, we see a hurdle, what does the data tell us? I think all business data is important because it tells you a story. How you interpret that story may differ, and it may tell people different things. For me, it’s important for me to look at the data, not only to help lead in the right way but also to help innovate and grow in the right way. Whether that be growing people or growing the business, the data is important, but the human element of it is always there.

You need to make sure that you’re looking at both in order to make the right decisions. Data is only part of the story. The humans that interact to create that data or make that data are also important. Going behind the data to see what that looks like from a human perspective is important.

SS: I love that. I know on the human side, one of the ways that you focus on this is by developing a sales council to support your enablement strategy. Tell us about that program. What did it entail and how did it impact your enablement strategy? 

MM: This goes back to that human focus part of it. What we learned from interviewing a lot of our sales personnel was that we were hearing things like, we need more experts, more SMEs teaching us. We need a better way to actually understand what we’re supposed to be doing. To me, that human element of people coming to us saying what we need is a data point. You take that human element and that data point and you say how do we fix that for me? 

There were two things. One, you always know that people in your organization are trying to move up or trying to better themselves, and ofte