Scaling a sales team is not for the faint of heart – for one, it’s not even that much about selling. In this week’s episode, we bring you insights from someone who’s done it not once, but twice.
When it comes to launching sales teams in hyper-growth startups, few people have walked the walk as much as Maggie Hott. Despite attending university at Santa Barbara, not too far from the mecca of tech that is Silicon Valley, Maggie never thought she would end up working in technology. She “stumbled” into it, as she told us, first as one of the earliest sales hires of Eventbrite, where she stayed for four years, and then into Slack in early 2015 as the first sales rep in the Bay Area.
At Slack, she rose through the ranks from an Account Executive to a Senior Enterprise Leader, and by the time she left Slack six years later, their revenue had grown from about $12 million in ARR to more than a billion dollars. Now, Maggie is the Director of Sales at Webflow, a web design tool that helps users design and build responsive, custom websites with no code whatsoever.
We recently sat down with Maggie to chat about all things sales – from laying down a solid foundation to hiring the right people and, finally, scaling the team into hyper-growth.
Here are some of our favorite takeaways from the conversation:
1. Look for the team players
In those early-stage moments, businesses should be focused on hiring people who are collaborative, who are always willing to jump in and help their colleagues out. How exactly can you spot them? When Maggie’s in an interview process, she likes to dive deep not only into the candidate’s proudest wins and the moments they went above and beyond, but also their mistakes and losses:
“During my interview process, one of the biggest telling signs for when I pass on a candidate is probing into why a deal was lost. What I’m looking for here is not if they can win or lose deals. I’m actually looking to see, do they take ownership of losing the deal? Are they blaming others? What did they learn from this last deal? How are they using this to improve? Above all else, the number one thing that I’m looking for here is a growth mindset.”
2. Invest in the proper tech stack
As operations scale, businesses need to handle an increasing number of deals. And so, at some point, most leaders start looking into ways to automate work so teams aren’t spending most of their time doing low-value, repetitive administrative tasks. Maggie is a big believer in technology to enable her sales team to perform better, and the sooner you build that foundation, the better:
“One of the first things I did coming to Webflow was take a look at our tool stack and ask, ‘What do we need to add? What do we need to change? What do we need to evaluate?’ It’s also important to purchase tools for scale. I mentioned this before with LinkedIn Sales Navigator – we don’t necessarily need it now, but when we’re three to five times the size, having these strong tools is really important.”
3. Do right by others
When it comes to core values for the sales team, Maggie makes it really easy to memorize. Customer first, then company, then yourself. People tend to look at sales as this very individual job, where you have your quotas and get your commission, but sales isn’t an island. And so, it’s crucial to foster team spirit, not only within sales but in cross-functional teams, too:
“How you work with your colleagues, especially your cross-functional partners, can really make or break someone’s success. Everyone’s building towards the same goal, so I like to see if you play nicely and how you get to the end goal together. You can be a great sales rep, but if you’re a jerk and others don’t enjoy working with you, you’re almost certainly not going to be promoted.”
Caught your interest? We’ve gathered a list of articles, videos, and podcasts you can check out:
- Intercom on Sales
- Everything we’ve learned about scaling sales
- Slack’s “radical convenience” approach to customer experience
- Top tips for job seekers from two badass women in tech with Kim Graves and Maggie Hott
- “Give away your legos” and other commandments for scaling startups
This is Scale, Intercom’s podcast series on driving business growth through customer relationships. If you enjoy the conversation and don’t want to miss future episodes, just hit subscribe on iTunes, stream on Spotify, or grab the RSS feed in your player of choice. You can also read the full transcript of the interview, which has been lightly edited for clarity, below.
Stumbling into tech
Liam Geraghty: Maggie, we’re delighted to welcome you to the show today. To kick things off, would you like to tell us a little bit about yourself and your background?
Maggie Hott: Absolutely. And thank you so much for having me here today. Let’s see, a little bit about me? I grew up in a really, really small town in Northern California, about 800 people. Went down to school, to university in Santa Barbara, which is in Southern California, and kind of just stumbled my way into tech. I actually thought I would end up in the non-profit world, but I was taking some courses at university, and this wonderful speaker who happened to be the CEO of a company called Eventbrite came down and spoke to us. And I just thought he was great.
I never really knew what tech was all about, but I decided to reach out to that gentleman, Kevin Hartz, and basically ask him for a job. And after a couple of rounds of interviews, I ended up finding my way to Eventbrite. I was the second SDR they had ever had. I spent about five years at Eventbrite, moving my way up in the sales organization. And by the time I left, I was a senior account executive.
“A similar thing to Eventbrite, I actually prospected my way into Slack”
It was about 2015 when I found Slack. And Slack was really, really new. I was just starting to think about account management, not even necessarily sales at the time. They had a couple of account managers out of Canada, but no one in the Bay Area. And so, a similar thing to Eventbrite, I actually prospected my way into Slack. I was hired at Slack as the very first sales rep based out of headquarters. And at that point, we were about 12 million in ARR. I was at Slack from when we were 12 million to over a billion. Pretty big growth. Throughout my time there, a little over six years, I went from being the top-performing account executive globally to moving into leadership to help build out our mid-market team out of the West Coast. By the time that I actually left Slack, I was senior manager of enterprise.
About four months ago, I came over to Webflow. I’m now Director of Sales, leading sales globally for Webflow, which is a really, really fast-growing startup. On the side, I do some stuff in the venture capital community, some scouting for a wonderful VC firm, Cowboy Ventures. I also do some formal advising for a couple of smaller startups. On a personal front, I live in San Francisco. I’ve got a 16-month-old daughter who seems like she’s going on 16 from her personality. And then I’ve got two really large mutt dogs, and my husband as well.
Liam: Which brings us to Webflow, where you recently started as Director of Sales. How is that going? What are you most excited about?
“It’s so much fun to build and scale companies these days”
Maggie: Man, there’s so much. I’m so excited about what we’re building at Webflow. I just feel so lucky every day, and I’ll tell you a bit about why and why I think Webflow and product-led growth companies are a really, really unique animal. They come with a unique set of challenges, but they’re also primed to be really successful. Here’s an example. Webflow has over 130,000 customers today, but we really only started spinning up the sales team about a year ago. And that’s because Webflow, even though it’s been around since 2012, it’s all been really driven by the self-serve organic motion that is of course layered on with great customer support and customer service, marketing, amazing product.
But now, what we’re really doing is building on enterprise to help amplify that motion. And we’re seeing a ton of success with it. Actually, just within the last year, some of the logos I’m allowed to talk about are the likes of Zendesk, Rakuten, Dell, MURAL, Lattice, Hoppin, Deal. These amazing companies are not only within the Fortune 100, but they are also some of the fastest-growing tech companies out there. We’re seeing really good growth. We will likely triple my org by the end of the year. We’re at 10 now, and we should end probably about 29 or 30, and that’s just for sales and sales development. And just recently, we raised 140 million in our Series B. We’re really just getting started. It’s so much fun to build and scale companies these days.
Scaling a hyper-growth sales team
Liam: Wow. That sounds really exciting. You moved to Slack as the first rep based out of San Francisco, and you ended up helping to build the sales org there. What do you think are the biggest considerations when scaling a sales team in a hyper-growth startup? Are there any pitfalls businesses should be on the lookout for?
Maggie: Yeah, absolutely. I’m actually going to answer that in two parts if it’s okay. The first is the type of people that you hire and what these people will do. And the second part is the tenure of people you hire. I think one of the biggest things to get right is who you hire for your immediate teams, but also who is hired for the teams that you’re directly working with. It’s really important to hire team members who were very collaborative.
For AEs in particular, in the early days, I’d actually say only about half of their job is selling. The other half is a variety of projects, from hiring, recruiting, building, working cross-functionally. It’s really important to have strong relationships with our cross-functional partners and to be a very clear communicator. You have to hire people who are really comfortable with ambiguity, and you have to hire people that have a great attitude because building a startup is definitely not the faint of heart. I always like to look for people who are willing to jump in and help others out, which is really, really important as you grow.
“The whole reason we needed a VP of Sales is that we hadn’t seen the scale in a way that a tenured senior leader had seen”
In terms of the tenure of people, I think it’s important to have a mixture of leaders who have done it and seen it before and really seen that scale and hyper-growth motion and people who are promoted from within, who’ve been at the company and know the product and the customers like the back of their hand.
Back in 2015 or 2016, we learned at Slack that we were going to be hiring a VP of Sales. All of us were like, “We don’t need a VP of Sales. We’re doing so well. What is a VP of Sales going to do for us?” But in reality, the whole reason we needed a VP of Sales is that we hadn’t seen the scale in a way that a tenured senior leader had seen. We ended up hiring Bob Frati. He came in when Slack was at around 50 million ARR, and he really helped build out the leadership team and helped us scale to over a billion. I genuinely don’t think we would have had the success that Slack has had if it wasn’t for bringing in tenured leadership from the outside because they must coach those of us who have been there for a while on excellence.
Lastly, in terms of pitfalls, I think it’s really important to build the foundation before you layer on the people. Something that makes me nervous is when companies just start hiring and loading and loading and loading on the people without a foundation there. That’s not going to set those people up for success.
“It’s not because we need it right now. But we’re going to need it as we grow and scale and it’s so much easier to get it right in the beginning”
One big thing is, and it sounds obvious, to make sure the tools and the systems are in place so that sales teams can be really successful. For example, over here at Webflow, we’ve invested in what I think is the absolute best tool stack possible. Even though some of it, like LinkedIn Sales Navigator, is really expensive, it just makes sense. And it’s not because we need it right now. But we’re going to need it as we grow and scale and it’s so much easier to get it right in the beginning than to try to come in and change it at the end.
Finally, in terms of pitfalls and the type of people that can detract from an org, I really try to stay away from people who have a lone wolf mentality, at least in the early days, because it’s so important to be really collaborative. People who are negative, who put themselves before the company or even the customer.
Other pitfalls in the early days, I think, are people who are very money motivated. Likely, the compensation structure is just not going to be figured out. It was actually just a few weeks ago that we moved our account executives at Webflow from a team number to an individual number. And of course, we introduced an accelerator, which is a huge win, and it actually took about two years from when I was at Slack before we actually formally moved to a comp plan. So if people are coming in just trying to make the most money possible, a startup is probably not the right spot for them because all of that stuff is still being figured out.
Lessons in hiring
Liam: Yeah, for sure. And you talked a lot about hiring there. Do you have any specific questions that you ask to understand if the person interviewing is the right one for the job?
Maggie: Many. Actually, these days, I’m in five to six interviews a day, so I ask a lot of interview questions. But I’ll touch on some of the core themes that I like to focus on. So first off, I really like to understand, what are their most proud wins? What are their toughest losses? I like to understand, especially for these early days, what these account executives have done that’s above and beyond their current role of just selling? I like to ask about the biggest mistakes they’ve made, about their proudest moments.
“One of the biggest telling signs for when I pass on a candidate is probing into why a deal was lost”
Something that is really, really important to me is looking at their career trajectories. I’ve actually found that the most impressive candidates are the ones that are promoted from within an organization and continue to grow from within versus the ones that are leaving and hopping every year in order to get a higher title or pay elsewhere. I also spend a lot of time digging into why people make the moves they did because I actually think it really takes a full year to get good at selling a product and building a pipeline, and it’s a bit of a red flag if someone’s hopping after a year because it means their pipeline probably wasn’t where it needed to be.
Finally, during my interview process, one of the biggest telling signs for when I pass on a candidate is probing into why a deal was lost. What I’m looking for here is not if they can win or lose deals, I’m actually looking to see, do they take ownership of losing the deal? Or are they blaming others? What did they learn from this last deal? How are they using this to improve? And I think above all else, the number one thing that I’m looking for here is a growth mindset.
Liam: I think that’s great advice. As your revenue grows, your sales org becomes more complex and you will obviously need to evolve. So I’m guessing the needs change according to the different stages of the company, and that the first few sales hires are probably different than the 50th or 100th hire. What’s your experience when it comes to adapting the sales org to meet the different needs of the company?
“In the early days, it’s less about building the orgs within the sales team and more about building a really strong and sustainable foundation”
Maggie: 100%. And it’s a tough one because there are so many different stages within a company’s growth and tenure. It also depends on the product you’re selling. Is it product-led growth? Is it true enterprise? But I think the biggest theme out of all of it, in the early days, is that it’s really important to look for people that are Jack and Jills of all trades, for lack of a better term. I like to look for people who are comfortable with change, people that thrive. Something I like to say is people who embrace the chaos. There’s a lot of chaos in the early days, even from one to 100 of a sales org. It sounds silly, but I like to look for people who can make friends with just about anyone in the company, people who love working on different projects and initiatives.
I’m also looking for people who are willing to put in the grind and hard work. I’m very, very much a believer in work-life balance, and it’s something that I really reinforced for my org, but being at a startup is not for the faint of heart. And in the early days, it’s less about building all the orgs within the sales team and more about building a really strong and sustainable foundation. Part two of that is you continue to go upmarket and get bigger, and this is when things will naturally start to turn more into a true sales-focused store.
Once you have about 50 to 100 reps, at this point, it doesn’t make sense for everyone to have different side projects because that’s just not going to be good. At this size and scale, it’s really important to have processes and structure. Things like segments, ROE, territories – this is when you need to have this stuff implemented and locked down. It’s also important to have fully built out functions like ops with enablement teams.
“In order to effectively scale and grow, you have to give away pieces of your job”
If the listeners have not yet read, there’s an article called Giving away your Legos by Molly Graham. It is my single favorite article that is out there. Basically, what it talks about is that in order to effectively scale and grow, you have to give away pieces of your job. This is the element of giving away your Legos. And it’s going to feel really challenging. It’s going to be hard to build something and then give it away or give it to a new team or a new department. It’s hard to let go. But letting go is good because it means the company is growing, and it allows each individual to take on a new and broader scope.
For example, when I was at Slack, in the early days, I actually helped build out our entire EBC org, actually wrote the job description for our director of global EBCs. I helped to build out our EDU org, our non-profit org, our SMB org, our compete programs, our outbound motion, and all of these things are actually all now full functions today at Slack. Being able to start all of those things and then give it away was a tough pill to swallow, but now I’m able to step away and take a look back. And what was once upon a time my little baby is basically now a full-fledged adult. And that is a really, really powerful thing, to now watch all these orgs grow and flourish.
Choose the company, not the role
Liam: It’s a fantastic thing to be able to watch that. You recently left Slack after six years and moved to Webflow. Do you have any advice for our listeners on how to choose their next role or company?
Maggie: Yes. This is something really near and dear to me, as I’ve lost many candidates too, as I go through the process. And I always want to do a retrospect with that candidate, learn where we missed out, learn where they went wrong, and it’s really interesting to hear and see why candidates make the choices they made. I would say my biggest advice for this is to choose the company, not the role. So often, people are enamored with titles and promises of higher OTE, and I often see people picking a company because of promises of these things. Because maybe they’ll get an enterprise account executive title at a brand new small company versus a mid-market title at a more established company.
“We saw people interview and turn down for promise of higher title or OTE elsewhere only to find them back in the interview process a year later”
When actually, in reality, oftentimes those mid-market deals in an established company are going to be much bigger and more complex. We saw this happen all the time at Slack. We often saw people come, interview, and turn down for promise of higher title or OTE elsewhere only to find them back in the interview process a year later in some cases.
I’m a firm believer that if you choose a great company and you put in excellent work, you will actually be rewarded with promotions and your career is going to continue to flourish. If you go to a company that doesn’t end up being successful, you’re often going to have to start over somewhere else, probably in that exact same spot, maybe even a year or two later, and you’ve now wasted that time. Overall theme: choose the company, don’t choose the role, and the roles will follow.
Liam: Great advice. And how’s your sales team at Webflow structured? Is it different from the way things used to work at Slack?
Maggie: Actually, what’s funny is that the team at Webflow is nearly a carbon copy of how it was structured at Slack in 2015 or 2016. Right now, at Webflow, we’ve got one level of account executive and the majority of our opportunity is actually inbound. In fact, we’ve just started building our outbound motion. Every single AE is far surpassing their quota, which I think is really important for the early days, because as I said before, AEs are doing so much out of the scope of just selling. It’s important that they’re able to attain their quota so they can also help focus on other areas and other projects.
“Another thing that’s different at Webflow versus Slack when I started is that Webflow has really big partnerships and agency models”
At Webflow, we’ve actually just hired our very first two CSMs within the last few weeks. We’ve got three solutions engineers. And as I mentioned before, I’m likely going to triple the org by the end of the year. And then what’s really, really exciting is that I’m launching a brand new sales development org based out of Denver. We’re launching in two weeks, and that is going to grow our sales org by 50% overnight because we have five folks starting on one day.
The other really interesting thing is we’re seeing a lot of traction from international. Despite not ever doing any marketing or any targeted outreach, we’re seeing some really incredible traction from Germany, from Australia, just all over the world. At some point, probably in the next year or two, we’ll really start to think about going global.
Another thing that’s different at Webflow versus Slack when I started is that Webflow has really big partnerships and agency models. We have thousands upon thousands of these clients and companies. Basically, they’re building off Webflow and helping to service the clients that are using Webflow. This is helping to reinforce the stickiness and retention and success of our product. It’s also a really good revenue stream. And a ton of fun! Our partners are amazing – they’re just a bunch of really, really neat people all around the world that are helping to really bring up and build the Webflow mission.
Culture add over fit
Liam: Something our CEO Karen Peacock used to tell us was that she saw this one misconception about sales in a lot of the high-growth businesses she encountered over the years, that all there is to sales is maximizing revenue. And while we were scaling our sales team at Intercom, we spent a lot of time thinking about our sales culture, about the core values that absolutely every hire had to live by. And it was about putting the customer first, not revenue, being personal in the way we communicate with prospects, and doing impactful work. What are your non-negotiables when hiring salespeople?
Maggie: Yeah, absolutely. At Webflow, we have core principles that we live by. The way I like to think about this and coach the team that it’s customer first, then company, and then yourself. It’s really important that account executives also become the voice of the customer internally because we are those front lines. We are sharing the feedback that customers have and their product asks and their successes and their failures back internally.
With all of this in mind, when I think about hiring salespeople, I want to see if the future hires will put others before they put themselves. Will they think about the customer first? Will they help them solve their needs, or are they going to try to maximize and squeeze out as much revenue as they can? I am a firm believer that revenue will follow good karma, whether it be in the form of references, referrals, renewals, expands.
“I believe the world is small, and it’s really, really important to always put others first because people will always remember how you made them feel and what the experience was that you gave them”
Here’s a funny story that happened to me just a few months ago. When I was an AE at Slack, I sold to one of the world’s largest athletic retailers. And they ended up being on Slack, growing the entire company to over 100,000 people in Slack. And they’re really one of Slack’s major success stories right now. And lo and behold, that exact same retailer, and ironically that same exact team, came into Webflow inbound about two months ago. And it was just so fun, getting on that call and being like, “Hey, remember me? Here I am again, different company.” But with this, I believe the world is small, and it’s really, really important to always put others first because people will always remember how you made them feel and what the experience was that you gave them.
“We spend more time with our teammates than we do with our families, so it’s important to hire people who are going to be great humans to work with”
Liam: 100%. And how do you make sure that culture also scales?
Maggie: One thing, and I always like to call this out is, I actually don’t love the word culture fit. People talk about culture fit a lot, but I think culture fit implies that culture is stagnant and that it’s not evolving because it’s just fitting into something. I like to think about it as a culture add. As I look for new team members, I encourage all of my hiring team to really think about what this person will bring to our team from a culture or a skills perspective that we don’t already have. How are they going to grow? How are they going to help us shape and flourish? And what will we learn from them? What will they learn from us?
We actually spend more time with our teammates than we do with our families, so it’s really, really important to hire people who are going to be great humans to work with. You don’t have to be best friends with them, of course, that’s nearly impossible, but you do have to be able to build a foundation of trust to work through difficult times. And I think that part is also really important to culture and scaling.
Building a solid toolbox
Liam: And obviously, as operations scale, you need to be handling more and more deals. And let’s face it, it’s not exactly scalable if you just keep hiring new people. So at some point, most sales teams start looking into ways to automate work so that people aren’t spending most of their time doing all that repetitive administrative work or other non-selling tasks. How are you tackling this issue at Webflow?
Maggie: Oh my gosh, I could not agree with this point more. It’s something that I’m constantly thinking about because there’s nothing worse than having to spend a half-hour doing an administrative task behind the scenes that could have been avoided. So I like to think about how to make things easier for account executives, SDRs, our cross-functional partners. Especially as we’re adding in all these new functions, like solutions engineering and customer success. Again, going back to that foundation needing to be really, really solid.
“One of the first things I did coming to Webflow was take a look at our tool stack and ask, ‘What do we need to add? What do we need to change?'”
I’ll spend a little bit of time on this one and break down how I’m thinking about this from a tooling but also from a people aspect. First, as I think about tooling, it’s really important to purchase top-notch sales tools to help teams do their job better. I am such a believer in great sales tools and technology. One of the first things I did coming to Webflow was take a look at our tool stack and ask, “What do we need to add? What do we need to change? What do we need to evaluate?”
For all of those out there listening, you hear that people are most likely to buy tools in their first 90 days, and I could not agree more because I’ve basically been on a tool buying spree the last couple of months. It’s also really important to purchase these tools for scale. I mentioned this before with LinkedIn Sales Navigator – we don’t necessarily need it now, but when we’re three to five times the size, having these really, really strong tools is really important.
The four tools that are core and dear to my heart, that I literally would not work anywhere without, are Gong, Troops, Sales Navigator, and Slack. For anyone who doesn’t have these tools, please go get them immediately. I am probably Gong’s biggest fan, and it’s not only because it’s a great tool for call coaching, but Gong is helping our reps ramp a lot faster than ever before. All of a sudden, they’re able to start on week one and listen and basically have a front-row seat to an entire sales cycle from start to finish. I like to tell my leadership team to go do daily Gong walks. I also like to Gong and puzzle, Gong and clean, but basically, I always have Gong attached to my hip.
“We use Slack to collaborate with our external customers. In fact, we just closed one of Webflow’s largest deals directly working within Slack”
Another one that I love, which we just finally wrapped up the purchase for at Webflow, is Troops. Troops is amazing for automating Salesforce hygiene and Salesforce tasks. You can also celebrate wins, it builds culture, and ultimately, Troops helps the reps keep their Salesforce more up to date, which is a common thing we hear about that is never happening in Salesforce. I don’t either. Troops directly integrates with Slack and helps with that. And it also notifies us in real-time when leads come in, when wins come in – it’s a really cool tool.
And obviously, Slack is so crucial for sales, but it’s really important to set it up correctly. We have different sales wins channels where we actually have the whole company in there seeing what the sales team is doing and telling their stories of these customer journeys. We’ve got account-specific channels, and we actually use Slack to collaborate with our external customers. In fact, we just closed one of Webflow’s largest deals to date from directly working within Slack. Even now, in post-sale, we’re still working with them directly in Slack. And by doing that, it just breaks down some of the barriers of email and just makes the process a lot more human.
We still have a long ways to go at Webflow. I’m not saying everything’s perfect by any means, we have a really long roadmap of things to build ahead. On the people side, as I think a lot about scaling here too and removing out some of this administrative work, we actually have an amazing finance team that has been helping to offload a lot of the burdensome administrative tasks that the account executives used to have. We’ve got an amazing data team and marketing team who are constantly thinking about how to get leads faster. One really interesting lead engine for Webflow is our self-serve database. Essentially, if there are 130,000 customers in there, how do we understand which ones we should be starting to build relationships with? That’s something data’s thinking about.
“Sometimes, the answer is to throw more people at the problem. You just want to make sure that if you’re doing that, it’s very high value and it’s something that can’t be automated”
We also just hired a world-class enablement leader who is already completely changing how we’ve always done onboarding. And she’s thinking about how to make our reps ramp and sell more effectively. I think it’s also important to build strong cross-functional relationships, not be afraid to ask for help, but also quantify what that help will do. In this case, we found out our account executives were spending hours provisioning these enterprise customers, and it was really convoluted. We were able to go to our VP of Finance and say, “Hey, Yvonne, our sales team is spending hours doing this for every customer win. It’s high risk of things going wrong, it’s a very sensitive thing. We’re logging into Stripe, we’re having all these different backend things. Can your team help take this over? And that’s going to free up more time to sell.”
I think it’s important to have those relationships, but also, sometimes, the answer is to throw more people at the problem. And that is actually okay. You just want to make sure that if you’re doing that, it’s very high value and it’s something that can’t be automated because people are actually a company’s most expensive asset.
It takes a village
Liam: I want to talk a little bit about collaboration in sales. People tend to look at sales as this very individual job. You have your quotas, work your deals, get your commission, and so on and so forth. How can you make sure you create a good team spirit within the sales team but also with other teams like engineering, lead generation, and customer success that are also obviously an important part of closing deals?
Maggie: Huge! And we couldn’t do it alone. It really, really takes a village. And a lot of the team spirit is going to be created by the people that you hire. The manager’s role is to help foster it, but it’s important to create a culture of openness and inclusivity, especially in this remote world where we’re not all there on the sales floor together. It’s important to create a culture of candor and constant feedback for each other.
Something I did at Slack, and then I have my more senior AEs do here, is they take on all these extra credit projects. For example, my two most senior account executives are involved in every single hiring panel for every feature AAE and sales, and managers too. I think it’s really important to give your top performers stretch assignments because it’s going to help them not only stay engaged but be prepared for their next role, whether that role is management or a more senior account executive – maybe moving up to a different segment.
“I meet with my marketing team weekly, my director of finance biweekly, customer success leadership weekly, and enterprise product every other week”
In terms of that cross-functional collaboration, it’s important to have consistent cadences with those cross-functional teams. I meet with my marketing team weekly, my director of finance biweekly, customer success leadership weekly, and enterprise product every other week. Having this strong foundation for relationship building makes it so much easier if you ever need to work through tough issues and come to solutions.
The last thing is I think it’s really important to actually have a team dedicated to thinking about culture. At Webflow, and I borrowed this idea from Slack, we actually have a culture committee comprised of at least one individual from every single department within sales. They think about everything from celebrating birthdays to diversity and making sure everyone feels heard and that they have a voice. This should be sponsored by leadership, but I don’t actually think it should have leadership involvement. This should really be team and rep-led.
“People who maybe never worked with sales teams before can have a bit of a negative connotation on what sales is”
Just to wrap this up, how you work with your colleagues, and especially your cross-functional partners, can really make or break someone’s success. I think a lot about our internal brand, both for myself, but also for my org. Unfortunately, the reality is that people who maybe never worked with sales teams before can have a bit of a negative connotation on what sales is. So it’s important that sales works extra hard to build our brand and show the type of work we do for our customers.
And I can’t stress this enough, but the internal brand is one of the most important things for career growth and promotions. Everyone’s building towards the same goal, so I like to think about if you play nicely and how you really get to the end goal together. You can be a great sales rep, but if you’re a jerk and others don’t enjoy working with you, that sales rep is almost certainly not going to be promoted.
The AE’s work is never really done
Liam: For sure. In terms of boundaries between different roles, where does the job of the AE stop and the CSM begin? In your experience, should there be a clear handover?
Maggie: I actually don’t think so. I’ve seen it go both ways. I’ll talk about how we’ve done it at Slack and at Webflow, which has led to a lot of our success in customer attention – the account executive or the original seller doesn’t ever actually step off the customer. In a lot of companies, if I were an AE and sold a deal, I would kick it over the fence and send it to account management or customer success. And I actually don’t think that’s a good strategy. Not only is it a bit of a disconnect for the customer, but it also can incentivize bad behavior because the AE is not going to feel that same responsibility they would otherwise if they were staying on for the life cycle of the customer.
“It keeps the customer experience really successful because the customer doesn’t feel like they’re being passed around to all these different people”
So, for us, account executives stick around for deployment, launch, QBRs, upsells, expansions. And I just think that’s a really, really strong model to follow because it keeps everyone really aligned and it keeps the customer experience really successful because the customer doesn’t feel like they’re being passed around to all these different people.
Liam: But then, how does it work because the AE is obviously working on closing more and more deals? So how could they deal with all of these accounts?
Maggie: This is the heart of scaling right here. It’s thinking about these different problems. How do you tackle this so you don’t burn out the AE and so you make sure the customer is getting all the love and attention they should? For each account executive, there needs to be a reasonable amount customers.
“I cannot reinforce this enough – do not underinvest in customer success”
And it’s important to have substantial resources in customer success. I cannot reinforce this enough for those of you out there listening – do not underinvest in customer success. They are not just a cost center – they will actually help with retention and growth, and they will be leading these customers that will stay on your platform for years. This goes back to my earlier point of giving away your Legos or parts of your jobs. As salespeople, we need to be able to give away our customers. And with that, we need to give away some relationships.
Again, that’s a hard thing to do when you’ve worked for two years to build a relationship, and then all of a sudden you have to give it away. But that’s what’s best for the company as you think through growth and scale. That being said, there needs to be clear roles and responsibilities between AE and CSM for both pre-sale and post-sale. They should be directly aligned in what their roles or responsibilities are, so each one can divide and tackle what they’re best at.
Venturing into leadership
Liam: Just to wrap up out, what’s next? Have you any big plans or for the rest of the year?
Maggie: Oh man. Yes, a lot. The big one for us is we’re going to triple our sales org this year. Webflow is doubling, sales is just growing at an exponential rate, and it’s been really cool to see how our revenue is directly impacting the company. We’re also going to continue to go upmarket. A big part of our roadmap is thinking about how we can build out these features that large enterprises need.
Let’s see, what else is really big? I think just building a sales team so that every AE who’s not at Webflow looks at us from the outside and says, “Wow, I want to be a part of that. I want to be a part of that brand. I want to be a part of that culture.” I think we’re off to a great start with this mission, but we still have a really long way to go to keep up with customer demand.
Outside of Webflow, I’m advising and consulting for a few very exciting startups. Actually, two of them just raised their seed round. I’m helping them think through their sales and go-to-market strategy, scouting for Cowboy Ventures, which is one of the best venture capital firms out there with an amazing, amazing team behind it. I like to do some mentoring for First Round Capital, and I’m just really proud to be involved in all these orgs as I start to explore more about the venture world.
I can’t wrap up without saying that raising my daughter is really, really important. Watching her grow and be a really, really strong woman. I have really big aspirations for what she’s going to do and what she’ll be someday. I just can’t wait to see who she turns into.
Liam: Yeah. I’ve no doubt we’ll be talking to her on the podcast at some stage in the future.
Maggie: Maybe 20 years from now.
Liam: Yeah, exactly. This series is all about hearing how companies scale their growth. Before we finish up, I’d love to know the key event in your career that helped you scale professionally.
“One of my mentors actually told me that it takes three years of being in leadership to become a strong leader”
Maggie: I actually remember the exact meeting where it happened. I was in a meeting with Kevin Egan, our VP of Sales at Slack, and he started whiteboarding what my career could look like if I stayed and continued to grow in my account executive career or if I wanted to move into leadership. We talked about the pros and cons of both, and ultimately, what we came to is leadership is something that I should try out. I could always go back to selling at another point in time if I didn’t like it.
For me, the biggest thing in my career was moving into leadership, having never formally led before, and having really strong leaders to help me with that transition. That is the single most important thing about moving into leadership, having this tribe surrounding you and supporting you and that you can go to. I leaned on them so much. My first year in leadership was actually really, really hard. And admittedly, I don’t think I was the best leader for my team. I don’t think I knew what I was doing. There was a lot of growth and a lot of change. One of my mentors actually told me that it takes three years of being in leadership to become a strong leader. I stuck it out despite some ups and downs, and I worked really hard on myself to be a better leader for my team.
The second one is that my team at Slack was the top-performing sales team globally. I would have never been able to get there and have this type of success if it wasn’t for the strong mentors that helped coach me on how to get there.
Liam: Fantastic. So, lastly, where can our listeners go to keep up with you and your work?
Maggie: The best place is probably LinkedIn. I’m not super active on Twitter. Every few months, I’ll put out a tweet, but I’m pretty active on LinkedIn. Search for me on LinkedIn, I would love to connect with all of you there.
Liam: Brilliant. Well, Maggie, it’s been an absolute pleasure to talk to you.
Maggie: You too. Thank you so much for having me.