Sometimes, it only seems like Devon McDonald is running Sales and Marketing for more than 10 different organizations. In truth, Devon is a Director of Growth Strategy at OpenView Venture Partners, a Boston-based Venture Capital firm. The firm has invested in and advised an impressive portfolio of expansion stage B2B SaaS technology companies. Which is where Devon comes in. She works directly with key stakeholders – CEOs, as well as VPs of Sales and Marketing – at these companies to provide strategic guidance and sound advice. She was also voted one of InsideView’s Top 25 Sales Influencers in 2013, as well as one of the Top 20 Women to Watch in Sales Lead Management. In short, she knows what she’s talking about when it comes to sales and marketing, especially for expansion stage B2B startups.
We recently had the privilege of speaking with Devon on the challenges of “managing” sales and marketing for multiple different organizations at once, her status as a Certified ScrumMaster and what she’s learned from her experience playing Division 1 college basketball.
1) You work directly with key stakeholders within OpenView’s portfolio to provide strategic guidance. How is this different than running sales or marketing for just one company directly?
OpenView invests in B2B software companies at the expansion stage, and one of our big differentiators is that we have a team of full-time consultants who are dedicated to helping our portfolio companies get bigger faster – we call this team OpenView Labs. No one else does this in the same way that OpenView does, and within our niche we have become known as the expansion stage value-add VC.
Practically speaking, what that means is that at any given time, my colleagues and I are having conversations with upwards of a dozen portfolio companies at once. People often ask me what it’s like to work with so many different companies, and how we are able to quickly assess what their pain points are. The simplest answer is that we’ve seen it all before, which makes the task less daunting.
The reality is that since we’re sharply focused on investing in expansion-stage B2B software companies, we’ve come to understand the challenges that these businesses typically face. Even though each of our companies has a different product and sells into a different market, they all face common obstacles as they scale. Those commonalities make it easier to look at a new company and quickly identify the opportunities for improvement. From a sales and marketing perspective, for example, the biggest challenge I see is that most companies don’t really know their core buyer personas and these personas’ buying journeys as well as they could or should. And often times sales and marketing team are target to broad of an audience so their messaging is diluted and doesn’t resonate with their key buyers. We are able to work with these companies to resolve that issue among others.
2) What is the key to building a repeatable, scalable sales process? Why is this important for companies to think about?
Creating a repeatable, scalable sales process is essential for all companies, especially those at the expansion stage. The companies we invest in are clearly doing something right if they’re already generating between $2 million and $20 million in annual revenue at the point at which we invest, but we know that to help them reach the growth stage, they need to have great sales processes in place. The way that we’re able to help them create those processes is by talking to members of their team, looking at their data, and sharing the best practices that have worked for other companies that have a similar model.
The bottom line is that you need a sales process that matches your buyer’s journey. From there, it’s a matter of defining the process and getting buy-in from the rest of the team. It’s really critical that everyone is living and breathing it every single day. Once you have everyone adhering to the sales process and using your CRM in the same way, you can get the data you’re looking for.
3) A big focus of yours is hiring. In your opinion, what is the number one mistake sales organizations make when it comes to hiring?
Too many companies focus solely on having industry experience. We believe it’s far more important to hire someone based on their personal characteristics rather than the number of years on their resume. A lot of people make the mistake of thinking that a candidate with 15 years of experience selling for a big company must be great. But that’s not always the case. What works for one company might not work for the next. I’d rather hire someone who is extremely disciplined and process-oriented, than someone with all of the experience in the world.
At the expansion stage in particular, it’s important to find people who can handle change and transitions. When a salesperson starts at this particular stage of growth, he or she can expect to experience changes in as little as six months. If you have a sales rep who really struggles with change and who is more comfortable with the culture of a larger company where change doesn’t happen that often or that quickly, he or she’s probably not going to be a good fit.
The market for top salespeople has also become incredibly competitive. Hiring can take a lot of effort and energy, and it’s easy to get burnt out. That’s why it’s important to network, recruit, and interview on a regular basis, so that you have a pipeline of talent when you need it. It’s also a good idea to always keep a req open on the team to not only attract additional candidates, but also keep your existing reps motivated. I’m a former basketball player, so for me I think of it like always having someone you can bring in off the bench.
4) That’s a great segue for us. You were a Division 1 basketball player at Colgate University – we’re big believers in the connection between sports and sales. What are the most impactful lessons from your playing career that still help you today?
It’s all about being part of a team, having a vision as a team of where you want to be, and living that vision each and every day.
Basketball seasons are long, and you’re not going to win every game or every practice. There are going to be some serious obstacles to overcome, but if you’re always thinking about the bigger goal and working toward it, it will help take you to the next level. My freshman year at Colgate University we weren’t that great, and we just weren’t jelling as a team. I don’t think we really knew what we were working toward. Sure, we wanted to win games, but we didn’t have a bigger vision in mind. My sophomore year, we went into the season knowing that we wanted to be one of the 64 teams to make it to the ‘Big Dance’ and the NCAA tournament. We talked about it all the time – practice, pre-game, post-game — and, because we had that vision, we were much more successful.
Similarly, companies and sales teams need to think about what their big goal really is. Is it to IPO? To get X new customers this year or exceed the revenue goal by X percent? When you make these overarching goals known on across the organization, it helps bring people together and focuses them on achieving it.
5) As a certified ScrumMaster, what tips can you share with our readers on how to improve their sales team’s motivation and focus?
Scrum is a big part of OpenView’s culture. Although it’s typically used by software teams to build product, here we use it in an operational setting, which is a bit unique. Scrum is very helpful because it gets you really focused on what you’re trying to achieve — whether that’s building a software product or hitting your quarterly marketing goals — and it helps you build a process and a roadmap to reach that goal.
We work in ‘sprints’ here at OpenView, which are basically work cycles that, in our case, last for a week. This is something I highly recommend that other teams do too. Basically, after setting our quarterly goals, we then plan out each week (or each of our sprints) around them. Each Friday, I plan and prioritize all of the tasks I am going to work on the following week, making sure that everything is aligned to helping me meet my quarterly goals. I know exactly how much time I’m going to spend working with a particular portfolio company, preparing for a webinar, or even answering these questions.
Things may come up the following week that I haven’t planned for, but having a prioritized sprint helps shield me from distractions. If someone comes to me with a random request, I’m able to push back and say that while I’m happy to help them, here’s how it will impact the other things I’m working on. Then it becomes a question of whether or not their new request is a higher priority than what I’m already working on. In most cases, it’s not.
Expansion-stage marketing teams get tons of requests. Having a shield in place like the one that Scrum offers, can be incredibly helpful.
6) With your work focusing on both sales and marketing teams, how do you think organizations can improve the relationship between both departments?
That’s always a challenge. I think the key is creating visibility into what everyone’s doing. With a tool like InsightSquared, it’s easy to see how marketing is contributing to sales, and vice versa. I think setting crystal-clear SMART goals when you’re planning on an annual or quarterly basis, and sharing them with each other, is the most important starting point. It sounds simple, but it doesn’t always happen. Marketing creates goals for itself and sales does the same. The problem is that the heads of both teams don’t always meet up and agree on what those goals should be.
I think when marketing teams use Scrum, it creates more visibility into what they are working on. Sharing your sprint and all of the tasks in your backlog across the organization creates a much greater sense of transparency. You don’t have to shove it down their throats, but Scrum can certainly bring clarity in terms of what people are working on and what goals those efforts are supporting.
7) Full disclosure, InsightSquared is a partner of OpenView. What did you see in us – especially through the lens of your portfolio companies – that led to this partnership? How big a role do sales and marketing metrics play when you’re advising your portfolio companies?
We’ve had a relationship with the executive members at InsightSquared for a long time. Fred was formerly in the VC world himself, so he’s pretty connected with some of our partners. As a result, we had a lot of trust in the executive team at InsightSquared from day one.
I think one of the things that caught our attention and got us excited about InsightSquared is that it’s clear that Salesforce.com is lacking when it comes to being able to demonstrate certain attributes of sales and marketing performance. It’s really hard to look at a Salesforce dashboard and understand the conversions at the different stages of the buying journey. With InsightSquared, however, you get a great visual representation of what Salesforce is unable to achieve within its own system. We’ve traditionally created Excel spreadsheets to try and capture this for our portfolio companies, but Excel is….well, Excel. Not everyone likes or is good at it, and you can easily lose focus and stop tracking the key metrics you need. InsightSquared, on the other hand, is easy to integrate into your sales team and to use as a daily tool.
When it comes to advising our portfolio companies, we tell them that it’s really important to be metrics driven and to track their conversions. It goes back to building that scalable sales model. You need to be looking at conversions and metrics to better predict if you’re going to hit your number and to know if and when to scale your sales team.
We’re always encouraging our portfolio companies to look at those metrics and to be more analytical in their approach. Where it’s appropriate and they’re looking for something that could be fulfilled by InsightSquared’s platform, we encourage them to check you out. It usually works out for everyone involved.
More about Devon McDonald
Devon is the Director of Growth Strategy at OpenView Venture Partners, a Boston-based venture capital firm focusing on expansion stage B2B SaaS technology companies. She has built over a dozen inbound/outbound lead qualification (BDR) teams for OpenView’s portfolio companies, while advising on building scalable sales processes, identifying target segments and more. She is a certified ScrumMaster (CSM) and was named one of InsideView’s Top 25 Sales Influencers for 2013.
