Episode 135: Sheryl Floyd on Bridging Organizational Gaps Through Empathy

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am 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 they can be more effective in their jobs. Today I’m excited to have Sheryl Floyd join us from Papaya Global. Sheryl, I would love for you to introduce yourself, your role, and your organization to our audience.

Sheryl Floyd: Hi, Shawnna. Thank you. I am the sales enablement and product marketing manager for Papaya Global. We are a SaaS platform for global payroll and organizations that are expanding and hiring in other countries. The unique thing about my organization is that we are in hyper-growth mode, despite all of the pandemic going on. I’ve been a remote employee starting about eight months ago. The majority of our workforce sits in Israel where our headquarters are, so this has also been a unique experience for me not being where the headquarters are located as well. I would say about 75% of my time is supporting the sales organization, and about 25% of my time is supporting their product team in terms of go-to-market activities.

SS: Sheryl, I’m very excited to have you here today. Thank you so much for taking the time to talk to us. Now, you have a unique background. Your career path has brought you to sales enablement through a bit of a unique journey because you actually started your career as a high school teacher. Tell us about your journey from being an educator to working in product marketing and sales enablement.

SF: Yeah. I spent about 15 years as a high school teacher. I taught fun stuff. I was a media teacher. I always joked that if I could hold the attention of a room full of teenagers, then I could surely train and work with adults in the same kind of fashion, so surely it can’t be as hard. While I was a teacher, I was always keeping up with things like video, web design, photoshop, whatever the latest technologies were to keep my students updated of the current trends in media and journalism.

I actually went back and got a second master’s degree in instructional design, and I found that I really loved doing this media myself. I thought I would just go out into the real world and try it. My first role after teaching, about 11 years ago, was working with a little boutique firm here in Austin. I was thrown into creating sales training for a really technical role. And it was just eye-opening for me. It was almost like getting an MBA or computer science degree at one time, but I just fell in love with technology and the training part. From there, I landed in areas that really allowed me to hone my skills in product marketing or customer marketing and sales training. So, it’s this all kind of been utilizing those media and journalism skills.

SS: I love that. What is it about sales enablement that inspired you and made you want to make this career switch? Why are you passionate about your career in sales enablement?

SF: I think it goes back to why I wanted to be a teacher in the first place of just having an impact on others. This to me is very similar after having taught for so many years and leading statewide organizations for other teachers and things like that. I just really felt like another challenge was out there for me. So just having kind of that servant’s heart was where I really felt I could help others in even different capacities. One of my early roles was really in an amazing, transparent company where they had very open-door leadership. It was very easy to work with others. It was a supportive environment and I decided this is the way it should be in work. I wanted to make sure that I could influence other organizations in that same way. I felt like, what are my superpowers in that capacity is what I would call a gap filler.

I tend to try to find what that missing piece is from a current process or customer experience and just figure out a proactive way to get it done or to stay ahead of the needs of my organization. So just having that empathetic view of what can I do to help, I think has served me. It’s kind of kept my passion alive for helping others. I would say the other kind of thing I love doing is knowing how to connect one piece of an organization of knowledge from one part of the organization to another, how can I be that channel so that people across the business know what’s going on. It goes back to that open door, understanding or making it easy for things to happen. That’s where I’ve kind of felt like I could make a difference, just having those kinds of empathetic powers, I guess you would say.

SS: Absolutely. You definitely need that for a role in enablement. Now, how do you leverage the skills that you learned as an educator in your career in sales enablement?

SF: It’s almost like something I could do with my sleep. I kind of joke with people curriculum development and assessment experiences are just things that you learn to do so quickly as a teacher. But I think aside from that, it’s really starting with the end in mind. Like, what is it at the end of the day that you want to be accomplished? Whether it’s a goal of training or of a message or of communication, keeping that in mind and then walking yourself backward and marking the key milestones that you want to be accomplished in order to reach that goal. It is so, so simple as something like, what does an objective look like?

It’s like by completing this training session, you’ll understand X feature, how to sell it and right fits into your current selling process. So, if you’d just kind of keep that very simplistic goal, and then at the end of the day, did you accomplish that by whatever assessment or methodology you applied to that situation? It’s just a very natural segue from education to training for me. I would say the other thing is what I would call audience empathy. How do I gauge a specific persona or group? Whether it’s a group of teenagers or a group of adults, maybe it’s a marketing group or a cross-functional group. How can you kind of reach them where they’re at in that specific time? Is it via being interactive? Is it understanding that they’re there to gain knowledge? Is it there was an update? Just having kind of that reason for speaking to them and meeting them at that level, I think is a really important skill that you can transfer from teaching to training or enablement.

SS: Absolutely. I love that. How has your approach to training and educating adults in a corporate setting maybe different from how you approach teaching children or young adults?

SF: I don’t know that it is that different, I think it goes back to knowing your audience. What is it that you’re trying to get across to adults or how is it that you can really understand their needs? It’s a very similar situation. I think the main difference though, is having that knowledge transfer, it’s more relevant for adults in a way that they act to apply to their job. So, they’re obviously getting paid for what they know and what they can do. And high school students, I think apply their knowledge to maybe a task or an assessment, but I think both of them are building on foundational knowledge and then helping them to connect the dots in order to build on that for future enhancement or skills, or maybe even a promotion or increased job responsibilities.

SS: I think you’re spot on. So, in addition to your background and teaching, just to pivot a little bit, you also have extensive experience in product marketing. In fact, your current role you’re responsible for both enablement and product marketing, which is a lot of responsibility let me just say, coming from a marketing background myself. So how do the responsibilities of both intersect and differ?

SF: I think in both respects that they are at its core, kind of a hub for being that intersection between product sales and marketing and those respects, they are very similar. I can think of using that kind of hub situation to accomplish more than just one goal, especially when it comes to supporting multiple teams. So, going back to that empathy feeling that I have for a customer understanding for instance, if you understand how your customer or prospect is either consuming a product, or what is their understanding of your offering, both sales enablement and product marketing roles are similar in that as a big picture thing, how is a prospect perceiving or messaging during their journey? It’s an example of that.

So, if you have a really good understanding of your product messaging, if you’ve already got an understanding of what your sales messaging is, then you can really identify in both scenarios how to best support that prospect. And with that comes your enablement activities for sales. I would say the second part of that is having feedback loops for your product and marketing teams. So, in both cases as a product marketer, I can take those sales conversations and go back to the product team and help them identify where these messages are landing well with our customers or prospects. The second part of that is, like I said, being a hub of the intersection of product marketing and sales, keeping that line of communication open so that when sales conversations happen, we can provide feedback loops back to product and marketing. At the same time, sales can also request specific marketing collateral that they are needing in order for a specific maybe campaign to land better with prospects.

So, it’s sort of making those cross-functional connections happen. Along those lines, I think it’s similar to keeping engagement with external audiences as well. So, how can we make sure that our customers are getting the right information in customer newsletters? Or what can we learn from when last interviews from our customers and what are the industry report saying that we can leverage? So, it’s using all of that customer knowledge and intel also keeping in the back of our mind what our competitors are doing as well. A lot of those things to me are relapsed. So, it just depends on what it is I’m doing at that moment, whether it’s a sales enablement activity or product marketing activity that sort of resonates with whatever knowledge or data I’m using or reporting I’m using at that moment.

SS: Absolutely. In closing, how do you balance wearing two hats and effectively delivering initiatives for enablement and product marketing?

SF: I don’t think I’ll be doing this forever in both roles, but I would say since we are like doubling and tripling our growth year over year at the moment, I think what we’re doing is building that foundational process and channel alignment in order to kind of stand up these two functions. Currently, I report to the VP of growth and as we grow, obviously the majority of my time is spent supporting that growth and our sales organization in terms of onboarding and training and ongoing needs and communication around our product and marketing activities. At the same time, part of my job is providing those kinds of critical communication needs across the organization and identifying what needs to be done like back to that gap, filling to not only support the sales team, but also to support the rest of our organization with foundational understanding of our customers, our competition and our processes.

Just building the foundation to make sure that the rest of the organization can grow as needed. I would say the other part of that balancing act is really making sure that we are keeping our reporting and data analysis needs up to date. And what I mean by that is making sure that I can utilize the data in different ways, but this is the same data, regardless of I’m a product marketer or a sales enablement manager at the time. In both roles and need to understand the customer and why we’re winning or losing deals and so a lot of that value I think can translate across both roles.

SS: Well, Sheryl, thank you so much for joining us today. I enjoyed learning more about your background and the very interesting career path that you’ve taken in your time to get to sales enablement.

SF: Thank you so much.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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