Erin Osman is the Head of Revenue Enablement at Procore Technologies.  In this conversation with The Collaborator, Erin explored her thoughts on process optimization, Revenue Enablement, and the importance of frameworks.

Some of the key points worth noting:

1️⃣ Erin’s team supports nearly 1000 customer facing teammates with a team of 12 (plus two open headcount).

2️⃣Good reminder that process optimization requires teams to look at qualitative and quantitative insights and maintain a focus on outcomes.

3️⃣You can’t boil the ocean.  Pick a couple of key priorities and execute on this.  If you try to take on too much you will simply do an inadequate job at a lot activities versus doing a great job at 1 or 2 things.

Audio Transcript

Unknown Speaker
Aaron,

The Collaborator
could you introduce yourself and tell us a little bit about yourself?

Erin Osman
Absolutely. Well, first of all, thanks for having me. Congratulations on 131 episodes. It’s amazing. A lot of great thought leadership in that and so honored to be here as well, especially as the last of 2020. Ready to go to 2020.

The Collaborator
You said, Well, on LinkedIn, the last of something on 2020 is a good thing.

Erin Osman
Celebrate. Forward, let’s move forward. All right. So um, yeah, a little bit about myself. So Aaron Osman, I’m the head of revenue enablement at Procore technologies. And I have been there for just about four months. So it’s an amazing company. So happy to be there. The people I work with are incredible. But a little bit about my background. So I think what I love about enablement is you have people that come from different, different backgrounds, different strengths. My I’m in the group of people who came from sales. So I started my career in sales at two different startups, which was great because I saw that tremendous growth, but also you’d wear so many hats early in your career. And company, spent the last 12 years almost 12 years before this at Dun and Bradstreet. And so also got to see her parts of the business, many customer facing roles in sales and CS, and then moved into enablement in 2015 is 2015 to five years now. And it was more product aligned at that time. And through an org change, we got to move over and start the the true sales enablement function there. So you

The Collaborator
otter delight, what kinds of things were you doing, Aaron?

Erin Osman
So it was channel enablement in the product channels. So it was more specific to aligning with product enhancement and working with specific customers on the needs and enhancements and changes and product mapping. But then also still, there was a component of making sure that our stakeholders, our sellers at the time had the information they needed with those products.

The Collaborator
Got it. Interesting. Yeah, sorry to interrupt you. But that was interesting.

Erin Osman
Well, good. Yeah. So then moved over, in sales enablement, worked on one line of business there, really, you know, got to learn year over year on how to scale that and have started at one place, get that going. And then once that foundational build on top of that, and build on top of that. And so in 2017, I took over running that team, and continue to scale it out a little more and add some some new components to our enablement system.

The Collaborator
That’s so cool. Now, what does your team look like today?

Unknown Speaker
So today?

Erin Osman
Yeah, so I have a team of 12. And we have, it’s a great, yeah, it’s a great, very, very well positioned to create a lot of success.

The Collaborator
So awesome.

Erin Osman
Yeah. So we have we have to open headcount to so channel enablement is posted and when will be posted soon for an instructional design team. So that leads to how it’s designed. So we have a team that focuses on learning and development. And that is really in three components. So we have our instructional design team, which and growing out more focus was just able to promote an internal team member to lead that team. So very exciting. Yeah. And then we have three team members who focus on onboarding. And we have two team members, one that focus on manager enablement, ongoing enablement, and then one that’s a sales coach. So also a great asset to have on the team. Yeah, a team that focuses on content management and communications.

The Collaborator
Fantastic. How many people are you supporting? You know, roughly,

Erin Osman
it’s right about 1000. So we support the entire revenue organization, a very, very big fan of, you know, I think when I started in sales enablement, I had this idea of, you know, in marketing, we have a spend in the marketplace to get our name out there. And we’ll make sure that we continue that conversation with our sales team members and the prospects that we’re talking to. But it’s so important that the customer journey is consistent, and that value messaging is consistent across customer journey. So working for success teams and mentation teams, the support team, I think is a very effective and efficient and exciting way to do enablement.

The Collaborator
I couldn’t agree more. I love the fact too. I mean, with roughly 1000 people that you’re supporting, you know, ballpark 12 people is actually on the lighter side, you know, for for what it takes to support it, because I’m seeing about 50 being a reasonable average 50 to one. So you’re actually slightly under that ratio, even with the addition of a couple of people. So it’d be really cool to see you kick butt and continue to grow the team and do and do some amazing things there. Now, one of the things you mentioned to me Aaron was process optimization. And I get excited about that. I started my career as an engineer. So I have a really big dork hat that I wear. And I will bring it out right now, but talk to us about what you don’t take. So tell us about what that that means to you? And how, what does it look like in terms of reality?

Erin Osman
Yeah, so I’m the same way I get really, really dorky about process optimization, I get really excited about it. Um, so I think, you know, looking back on my career, I’m very lucky that one of my roles, my first leader role was leading a customer support organization that focused on multiple different projects and multiple offshore teams. And with that I learned a lot about I mean, just basic things, right? Like, looking at average handle times, and how do you staff to those? And how do you stack to income coming in the time, a lot of marketing organizations weren’t doing or enablement, organizations weren’t doing as much because we didn’t have that data. Now we do. So just learning that is something that stuck with me through my whole career. And what I’ve found is if you look at, if you come into an organization, first, you have to understand the human element behind it, like number one, sit down with your people sit down with your stakeholders understand, it was only so much you can understand at the beginning, but understand, like, what is their day to day look like? And what’s important to them. But then where can you find data? Like what is out there for you to understand, like, what’s happening now? How are we? How are we impacting the business, whatever that role may be in enablement, obviously, you want to look at outcomes for the customer. But look at the data, look at where there’s opportunity to create efficiency, and then start organizing around those outcomes being very clear about the outcomes, the big fan of the rule of three. So while I want to boil the ocean all the time, because that’s who I am, you can’t

Unknown Speaker
get it,

Erin Osman
it’s not possible. And it’s not good, right? Because you’re not gonna do anything, you’re gonna do everything halfway. So looking at like, Where are the biggest areas for impact? And then starting to align around those from a functional org structure? What tools do you need? What are you going to measure towards? And then getting that alignment from the business on how you’re going to make it happen?

The Collaborator
Let me ask you this, because to me, this is always one of the critical questions that that I find intriguing to hear how people are approaching it, how do you determine where focus?

Unknown Speaker
Hmm, I know because

The Collaborator
words, Aaron, look for places of inefficiency. And and that always makes me say, Well, how do you look for areas of inefficiency, because I think we all approach it a little bit differently.

Erin Osman
Um, to me, it’s a mixture of qualitative and quantitative data. So again, going back to that, that first place, understanding the human figure or working with the human element, right, so that’s it, that’s the greater business and that’s your customer. And understanding, honestly, just what I’ve done in both enablement, organizations that have been a part of is in starting, starting in those roles is talking to the stakeholders. So talking to at DMV, it was my sales team talking to here, it’s been the sales team, the CS team, the marketing team, and really just understanding, you know, what do you feel the gaps are? What are the pain points and getting that before really digging into the data? Because that drives where you can look where you might want to focus on what data you’re looking into?

The Collaborator
I would say no, smart, no, no, really smart. And I was going to ask you, because you’ve been there what you said four months. Yeah. And you have 1000 people you’re supporting. And it probably feels like 20,000 voices coming at you. With all these different wonderful opinions about priorities. It can be overwhelming. So hey, I’m impressed. You don’t have hair like me. It’s a challenge. It’s a job. That’s wonderful, though. So you want to start by serving everybody. You’re trying to support a cross section of those people and get their feedback.

Erin Osman
Yeah, yeah. And I think you bring up a great point, because the reality is, you can’t serve everybody at once. And that’s the hard part, right? You have to make decisions, you have a limited amount of time to get things done. But what you can do is make sure as you build out the program, you number one, focus on what’s gonna hit the needle the most or move the needle the most. And then to create a plan where you’re not forgetting about the entire organization, even if you’re starting with one piece of the organization.

The Collaborator
Brilliant. Yeah, absolutely. Now, did you come in and were you? This isn’t a bad thing told. We need enablement to move win rates or we need enablement to help with discounting or extra wire z, or do you through these columns. Conversation say,

The Collaborator
I think this is where I’m seeing we can have the biggest impact initially. Yeah. In terms of, and then how it impacted your thought about process and all?

Erin Osman
Yeah, I’m gonna answer that a little bit in a roundabout way. So please, yeah, that. So I was brought in to record a scale enablement because of the large the sizable growth and the fast growth of the company, right? It’s amazing. It’s so fun to be a part of. So I was I was brought in with a lot of autonomy, I was brought in as you understand the organization, think about your background frameworks, and then understand where you need to go. That being said, I always I truly believe that if you look at measurement for enablement, that last one always needs to align to business outcome and business objectives. And so when I look at it, I would say No, I wasn’t told that but as being part of the team that I’m a part of, which is revenue, operations, strategy and enablement. Absolutely, I am going to align to what the main drivers are internally for us. So. And I think if I said I wasn’t going to, there would be some questions.

The Collaborator
Why? I’d be curious, I’d be I’d be really curious if you said, Nah, they’re crazy. We’re gonna focus over here, because I’ve never seen that work. So I would have been curious to see how you do it. Yes, you were D reporting to like a CRL, or to the ops team, or what’s that?

Erin Osman
Yeah, so we call our team rose. And again, I just wanted to send revenue off gradually enablement, which is a great alignment. We have field Ops, we have marketing ops in there. So it really is everything from like, what is our strategy? And then how do we go to the team to operationalize that from a systems perspective, from a process perspective. And then in enablement, there’s a process systems and art, right. And again, all of those, but that’s my area. So then, my leader Carolyn reports, the CRL. So

The Collaborator
that’s really cool. Now, I gotta ask you, this 1000 people, for those of us that are sitting here and saying, Oh, geez, I support 10 sellers, or I support 25 revenue, customer facing teammates, or even a couple 100. The thought of the difference in our heads, probably from 200, or 100 to 1000 might seem amazing and awe inspiring. How do you come in? And I know you’re four months in Aaron, but how do you put into place a process that you can say, I can repeatedly scale this approach, so that I can really support the entire organization in a meaningful way?

Erin Osman
Yeah, well, that’s where my my dorkiness and my nerdiness comes out, I get really

Unknown Speaker
thought it was going to

Erin Osman
I mean, I love it. It’s, it’s a big puzzle to me, right? Because it is hard. But, um, but it’s also extremely rewarding. And I think, you know, for those of us drawn to enablement, we are we get excited about these things. Yeah, I will say the hardest part for me coming in four months ago is I’ve never met anyone I work with. And for me, I would normally start my role being out on the on the floor, like meeting with team members, even if it’s people who are normally from a home office, like people are getting together enough fit offices, that I could sit in a room with people. So that part has been really challenging, because I haven’t been able to scale my conversations as much as I would if we were not in this environment. But that being said, I you know, you and I have talked about this before, whether you are one enablement person, a team of 25, you have 10 sellers, you have 100 sellers, you have 10,000 sellers, process is extremely important. And we all deal with such similar things. And I know this from the enablement community that it doesn’t matter where you sit in an organization, or how large organization is we all deal with, how do we make efficiency and effectiveness? Right? Amen. Say that.

The Collaborator
But you’re right. And because the only thing I want to interrupt you on Aaron was, I think sometimes people think Well, no, I’m the training person, or I’m the whatever, you know, whatever the limited function that they’re sometimes brought in to handle, but you’re not it’s exactly what you said, at the end of the day. It’s about effectiveness, process scale, and all those good things. And if you don’t realize that you need to start looking at it that way.

Erin Osman
bakley. So again, I think when you look at 1000 they’re all to me, even though I haven’t been able to meet those team members are team members.

Unknown Speaker
Yeah,

Erin Osman
you’re all people who are here to better the business better the customer experience. You know, I really believe in it. Our product suite, the solution that we’re offering. And so when I look at how do I make their lives easier so that they can focus on their jobs? That’s when I look at Okay, how do you scale this and to scale this is takes the right functional design, the right technology platforms, and the right reinforcement and certification, honestly, because that’s the only way you can do that at scale, right? You have to ensure the knowledge transfer. But it doesn’t just stop at training. And I like that you brought up training, because that’s a little bit of a pet peeve of mine. When people look at enablement, and say, just raining, right, it’s so much more it’s no, it’s minimizing the noise for our team members of infamy for all revenue facing team members. So that’s three communication steps through content that’s through making my partners and marketing’s job easier so that we can focus on this full knowledge transfer for our internal teams.

The Collaborator
Now, you touched upon something that that I find fascinating, I’ve never had to go through starting a new job during a pandemic.

Unknown Speaker
And I don’t,

Unknown Speaker
thank you, I wouldn’t recommend it. I would

The Collaborator
wonder earth are you trying to scale those conversations? I know you said that’s the thing you’re struggling with most? Is it just constantly picking up zoom? Or the phone or whatever? and saying, Hey, can I get 15 minutes with you? Are you trying anything that’s working well, for you.

Erin Osman
Um, it’s a lot of zoom calls. I mean, it’s raining all day, every day. And it’s, it’s really starting with which I think you should do anyway, starting with kind of the executive leadership teams and kind of getting their insight. You know, what I really miss is just being able to meet people on the floor and have those informal conversations. And that’s harder to do. And I haven’t figured out how to do that. But I do. coming onto a great team, and my team has a lot of experience with the teams that we’re supporting. So I get a lot of insight from them too. on, you know, what they know what they hear. And I was a history major that has not left me, like your engineering has not left you. And so for me, it’s really always important to understand, like, what’s the background of this? Like, you know, what, when, how did we get to this place? And like, what was the thought process behind that?

The Collaborator
That’s really good when you’re starting out, as you are now. And you gave a lot of great insight here already. But I’m curious if you would phrase it or add anything else to it. If I’m another enablement persons in a similar situation, as you are right now, Aaron, what would you advise they do in the first four months? You know, what are some of the things they like? Geez, in my opinion, you got to do these things to get started with a good framework or a good baseline?

Erin Osman
Yeah, I think this, this is one of those things. If I went back and did it again, I would do it a little bit differently. We all would. But you know, it’s like those things in your life where like, I know that it’s good for me, I know, it’s good to take a break and get exercise and good sleep. But then you get busy. And it’s like, that’s the time I needed the most. But you walk away from those those good habits. Yeah. So in the spirit of that, I would say, you know, I knew I had this time to really learn the business and talk to people. I wish I would have spent more time with my first one than that, of like really digging into some of the trainings that we already had more certifications more. And really having a deeper understanding of the work that the team had already done before going straight into those conversations. But I really wanted to have those conversations and understand, you know, where everyone else was and where their head was from enablement.

The Collaborator
But going back was hard balance. That’s a hard thing to balance.

Erin Osman
Yeah, it is hard, right? Because I also like, you know, I want to I want to do I want to do

The Collaborator
you want to have all those conversations you’ve talked about as well. Aaron, so I don’t know how you do. I don’t know the magic formula here in terms of how you balance doing both Well, I think it’s a very difficult tightrope to walk. And I’m sure you did a great job at it, but it’s a hard one.

Erin Osman
It is Yeah, I mean, I would I would agree with that because both are so important to understanding the business but also be building relationships so that you know how how you’re ultimately going to get the job done.

The Collaborator
Nice. Let me ask you this cuz you look sort of frameworks, or general pieces of process do you bring forth with you when you go to battle and enablement every day?

Unknown Speaker
Um,

The Collaborator
I asked it in such a bizarre way too.

Erin Osman
Oh, gosh, yeah, no, um, I mean, ultimately upset with us. So what’s the value that we’re bringing to the customer? And that, like, top of mind as you have every single conversation because again, it it’s about the customer journey, the customer experience?

The Collaborator
Do you actually take time to meet? Have you? Or are you going to at some point? do you envision taking time to meet with customers? They have those direct conversations, at least with some handful.

Erin Osman
Yeah, definitely. I have not, I will say I’ve used my network and Austin, some who are customers, some who are just in construction, to just talk to them about, you know, what’s, what’s their life, like, in their day to day. And that’s everyone from subcontractors, general contractors, and, you know, large construction organization. So, I’ve done that some of those, again, our customers, I would like the next phase to be more conversations with customers directly. But I do think that I mean, that’s something that Procore does so well, that I get so much of that to the content that we have. So I mean, that’s a huge props to our sales teams, our customer success teams, our marketing teams, like I got a lot of that information just through the work they had already done.

The Collaborator
Well, that’s the other thing I was gonna ask you, because I’m curious, you know, different companies are at different stages, whether they recognize this or not, in terms of really understanding what what the buyer journey is, what the customer journey is, we all think we really get it. And the reality is we it’s sometimes you’re closer than than not, but how do you do you seek to understand that as well? Have you taken time to sit down with marketing and customer successes that let me just walk through that entire journey and understand what those touch points are? Or is that something you don’t buy?

Erin Osman
No, I absolutely buy into it. And I do seek to understand it, I would say, you know, I’m not 100% there yet after four months, but understanding the teams you mentioned, right? So really through our our marketing teams, our customer success teams, our sales teams, all of those teams, like what is the journey that they’re taking? Because I have to align my enablement to that journey, right. Like I want to understand, like, what is their customer life like? And then also, when they’re going through the buying process, and the implementation process and making everything effective? I want to understand, like, what is going through their brain or their thought process, or their discernment process? Right, as they those decisions and like what other assets are out there? Where are they getting information from? That’s another big piece. Right? So it’s not just what are we saying to our team members about the value of the company, the value of the solution? But like, what are other third parties saying, right, so

The Collaborator
the floor, they’re checking all these other places? Right. Um, and that’s what I was curious if you sought to explore those different areas to, because to me, it makes a lot of sense. dig into that kind of stuff. And I’m especially interested because, you know, when we talk about the process improvement, Aaron, or that process focus, how much of that outside insight, do you pull into your approaches? Like, do you ever or in the past even looked at say, jitsu and been like, crap, I didn’t realize that was so painful? Not to say about a product, but maybe an experience they had?

Erin Osman
Yeah, no, I do. Um, and I’ll say pro for the very first team member I sat with was a customer success Rep. Because that’s what I want to hear. I want to hear that, like that person who has been in the journey, and then kind of back back into it. Right. So absolutely. Looking at, you know, how are how are we reviewed in not only technology platforms, but how’s the company viewed from a thought leadership perspective, you know, been able to connect with people on LinkedIn who I haven’t met, but that consumed the the thought leadership articles that are out there, a lot of great studies that we put out, but what are other people in like, there’s construction? dive.com has a lot of information. What are other people in construction? talking about? And does that align to what we’re talking about? Because if not, we need to, we need to hold on for a second, right? But if it does, it just enhances that story even more.

The Collaborator
You sound like somebody who’s had a year to have all of these conversations and do all this research. You’re clearly doing phenomenal. Aaron, what what advice would you put out there that we haven’t yet talked about? You know, we talked unfortunately, it’s already 27 minutes in and I feel like I only started talking to you. What What have we touched upon, that you feel is worth bringing up for people listening?

Erin Osman
Yeah, so I think um, I mean, we touched on this a little bit, but I think one thing I would just reiterate is you can’t boil the ocean. So When you walk in, you have to say like I’ve looked at it, okay, we have areas that we can improve on, we have areas that are kind of a little bit more innovative from an enablement standpoint. And then obviously, you have to look at the strategy, right? So it knows like, what are the three buckets that we’re really looking to so that we can align and be very clear on what our priorities are as a business? And then what are we promising? promising? What are we committing to the business that what are the numbers that we’re going to hit? Or what numbers or is this going to drive? Which I think the one thing we haven’t really touched too much on is measurement of enablement. And, you know, he did say, I think you need to align to the business outcomes. You know, there’s some caveats with that. One is, I would never take full credit enablement is one piece of the puzzle. We all as a business own the number. So, you know, maybe we have, I don’t know, a new manager who is doing something in their team that’s really driving results, and maybe we have demand Gen campaign that is just blowing it out of the water. And, and ultimately, in the best case scenario, it’s all of those things, it’s everyone is being successful and enablement is enabling that full touch. But if you’re not measuring the business outcome, if you’re not measuring what you’re doing to that business outcome, then what are you driving towards? So you either need to say, yes, we’re moving in that direction. But if we’re not, what do we need to change? What do we need to do? Or what do we need to evaluate to make sure that we are backing into that a little bit more, and this is less important to to the broader business. But when you look at the enablement scorecard, I do look at activity, I think that is just based on kind of just to understand like, what are we doing? Yeah, I don’t think more activity is better, right? I actually think the more you can get across with less activity is better. But then I also look at how are the tools being consumed that we offer? So what kind of content is being looked at what kind of trainings are being taken? Those kind of things, serving team members on how do they feel about the enablement that we’re doing?

The Collaborator
Keep coming back to that. I love that you keep coming back to that Aaron, the feel part is very important. Sorry, interrupt, please. No, no,

Erin Osman
it’s all good. But yeah, I mean, that’s not I mean, like we could, we could like throw water balloons at each other. And like, everyone’s like, yeah, that was fine. But like, that’s not gonna drive the business. I don’t know why I said water balloons. But ultimately, I want to be I want people walking

The Collaborator
on less bad about going into battle. Now. I feel bad, myself for saying that now. So thank you water balloons. Yeah, I

Erin Osman
want people to feel like it was impactful, it was engaging, and it was good, and that they learned that something that’s going to make them do their jobs better. And so to me, that’s how I keep my enablement. Yeah. And then also looking at when you look at certifications, like, what’s the engagement? What’s the pass rate? How are we looking at coaching? How are we looking at how we engage our managers, right, and our managers role in this. And then other business partners who are great partners, but help to drive home the message because even as a team of 12 of us, we can’t do this without partners in the business. But yeah, I’m

The Collaborator
so many great points there. And let me ask you this. Before we break, though, manager enablement, I loved at the very beginning, you touched upon the point that you at least have one person, maybe it was a couple focused on manager enablement? How do you look at that? What what are your metrics of success there? Are they still the same? I know that at the end of the day, it’s still the same business metrics. But when you think about what you’re trying to do, and how are you trying to help your managers, what do you think about?

Erin Osman
Yeah, I still, I still think it ties back to the same framework, you just look at a little bit differently of like talent, content, and communications really focused on on the managers, right. So making sure they have the information that they need to coach to talk to their team members to understand like, where to focus. And you know, we have done manager enablement, but that’s one of the places that there will be one of my main three priorities next year, right. So in a year, we can talk about this again, but I’m really looking at how are they coaching How are they engaging, you know, business results, but also, I think you have culture amp on at one point, right? Yeah. So even things like what is the engagement of the team members?

The Collaborator
Love though, Aaron, this was so awesome. And I feel excited that you stopped in shared your insight and that we’re ending the the first season of this show.

Unknown Speaker
Nice. talking to my dog.

Unknown Speaker
Sorry, thank you.

The Collaborator
No, it’s okay. I think it’s awesome. Look, that’s the world we’re living in right now. But anyway, Aaron, thank you so much for stopping by and sharing so much. Great insight. if people have questions for you is the best place LinkedIn

Erin Osman
again. Yeah, definitely.

The Collaborator
Yeah, we have a great community. Aaron is certainly in my opinion. I have a great deal of respect for everything that I see you put out there and and and after this conversation, I have even more respect Just doing so many great things in four months for a big team

Erin Osman
and now execute on them. That’s 2021. Right?

The Collaborator
That’s 2021. Exactly. We’ll talk at the end of 2021. about all the changes that have taken place. Thanks.

Unknown Speaker
I appreciate you. Thanks

The Collaborator
so much. And thank you everybody for listening. Have a great rest of your year and we’ll be back next year.

Unknown Speaker
Bye bye.

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