Modern Performance Profile: Katie Cartwright, Head of Fulfillment Sales at EasyPost, on how communication influences performance, public positive reinforcement, and more.
Katie Cartwright (LinkedIn, Twitter), the Head of Fulfillment Sales at EasyPost, began her sales career in commercial real estate. From there she moved on to Chegg, where she started as an Advertising Operations Specialist and finished as BP Business Operations Manager. Following her time with Chegg, she moved on to ADARA, where she was the Global Director of Sales Operations, running their sales planning and pre-sales support team and their sales operations. Now at EasyPost Cartwright manages the full funnel inside sales team. In this interview, Cartwright discusses how she monitors her teams at every stage of their sales, and how that attention plus her understanding of interplay between metrics and employee performance pays off.
What’s the secret to hiring for high performance? What are the most important characteristics you look for?
I look for a number of things; one of the most important is the ability to problem solve. I search for individuals who are solution-oriented and can think outside the box, outside of the script, if you will.
“We don’t want someone who just has sales experience and can sit down and crank. They can’t be just an order-taker. High-performance candidates are able to think about the big picture and understand context.”
That’s super important because I want people who can manage their own book of business and manage their own day. I want the kind of people who are able to see when they need to make changes and tweaks on their own, in addition to responding to the coaching and the guidance that I, and their peers, give them.
I use a blend of approaches, depending on the candidate, and how we found them. The main thing that I’m looking for is how they approach a problem. So I give them a number of different scenarios, and they walk me through their thought process to solving the problem.
“I don’t just want an answer. I want to know: how did they find it?”
Sometimes I ask them direct questions, sometimes we do role play exercises. I want to see them work through questions and think on the fly, to see what kind of solutions they can come up with.
The first two weeks are a sort of “boot camp” style of learning. The first week is very classroom-heavy with a lot of role-playing worked in, and we focus on really learning the product, learning the company, and how to get that first call on the prospecting side. The second week is predominantly focused on the carrying calls, running meetings, and moving deals towards the finish line.
“The most important aspect to onboarding is providing new hires with an understanding of expectations.”
We set goals upfront, as people come in, to make sure they have an idea of the full onboarding cycle. Then we introduce them to the metrics we watch and how we ensure that people are making progress towards specific goals throughout the cycle.
There are a couple of goals for any one-on-one. The first is to provide an update and an understanding of where someone is in terms of pipeline and performance. I want them to leave the meeting with a clear picture of where they stand. Secondly, I address any specific concerns, both about their immediate performance and with regards to their career progression. This evolves during onboarding and through the life cycle of a sales rep; the way I handle one-on-ones when someone first joins the team is different from how I handle them later on.
“I always aim to make sure that we’re on the same page when we talk about pipeline and deals, as well as their individual performance and performance within the team.”
In terms of agenda, I start the meeting with a check-in: where they are, statistically, with respect to their goals, their own quotas, and where they sit among their peers. Then we move into any tactical or strategic issues they want to discuss. I always make sure we address anything they want to talk about. The pace is dependent on the individual. Different people have different needs and respond to different methods of coaching and types feedback or constructive criticism.
We start with a weekly recap of where we are as a team and highlight the deals we closed or any big wins. We discuss any changes that might come up and then jump into a few specific statistics. As a team, we track three different major categories: one, opportunity signs and deals that are closing or have closed that week. This leads naturally into opportunity conversation. I have a full funnel sales team, so we focus not just on opportunity closes but also opportunity creation and progression. Then we talk about email volume and performance, to give people a sense of how their week looked relative to their peers. I think this is valuable, to demonstrate how behavior drives productivity.
Finally, we have a weekly contest—which changes each week. Sometimes it’s a product-specific or industry-specific training overview, or maybe we dive into a hot topic within the team. Some weeks, it’s more of a sales training exercise, roleplay, or, with newer sellers, pitch practice with collective feedback. Then we close by addressing any questions or topics or content that we want to circle back to in future meetings.
“I treat these meetings not just as a statistical recap but also an opportunity for learning and training exercises. They are a chance to build the habit of continually learning and developing week-by-week.”
We work backward from opportunity closes to opportunity creation and progression, and then to email performance. Our first round of prospecting is done over email, so we look at email statistics: send volume, open rate, and reply rate, and compare those to meeting sets. Our focus is week-to-week progression. A tough email week results in lower lead conversion, which in turn limits opportunity closes in future weeks. So in one-on-ones, we really focus on the individual progression through each stage. We look at how many leads are coming in the top of the funnel, and how they’re moving through the opportunity process and then the close process.
Then, we look at how someone has been responding to feedback—for example if in the previous week we discussed one element of the process and the person doesn’t seem to be getting through that barrier. Sometimes, sellers are really great at working through the top of the funnel, but struggle to get things across that deal line. So we talk through specific examples for each stage.
If someone is more senior and already effectively moving deals through the funnel on their own, already hitting their quota, they don’t need the same type of guidance. They don’t need that push. In those cases, my coaching style is more consultative, less step-by-step.
“When someone has been around longer, I ask questions and let them drive the conversation. What do you need from me? Where in your pipeline do you need help? Where are your gaps, where are your holes? What do you need more of? Right now, most of my reps are relatively new, so I tend to take the lead: Let’s look at the numbers, so we can determine where you need more guidance or coaching.”
The first month we’ll have longer one-on-ones. As soon as they’ve started creating opportunities–which for our deal cycle is within the first two to three weeks–we go through each one to make sure that they’re progressing it properly through the pipeline, approaching it in a productive fashion. I want to ensure that they fully understand each stage of the process. We really dive into the weeds. When a rep has been around longer, they know when a deal should be at 25% or 50%, or when a close is lost.
In team meetings we look at most of the same numbers and use them as fuel for healthy competition, to encourage people to want to catch the guy who’s one spot ahead of them and to keep up with their peers. By using our leaderboards–which show email performance, lead conversion, and opportunity stage progression–we’re also able to break into a less quantitative perspective:
“Hey, Josh. You had really awesome reply rates last week. You blew everyone out of the water. What did you change in your emails? What happened there?” We use individual successes as a team learning experience. And I probably already had that conversation with the person in his one-on-one. But asking those questions again in a team setting, after he’s had a chance think about them on his own, helps him to better explain his approach and techniques to the rest of the group.
My whole team sits in the same room right now, which is great for communication, in terms of idea-sharing. When a team is spread out, the Slack channel helps us maintain collaboration.
“Something that I like do is throw specific people a softball questions I know they can handle well. This encourages team members to share with each other and not rely on me for every answer.”
For example, let’s say someone has a use case that is a specific objection, or a funky use case on how to price something or and an outside-the-box way to answer a question a customer has asked them. If I know one of their peers has been through that issue recently, I’ll pass the question to them to promote an environment of communication within the group. When I get a direct message or specific emails from a seller, I almost always put it on the team channel for crowd-sourcing. Otherwise, I think that knowledge can get too sequestered.
There are a couple of big factors: you have to be confident that the individual can accomplish the task that you’re delegating and that it’s not going to take away from their core responsibilities.
I’m very conscious of making sure that I’m not going to interrupt their progress on individual goals. The key is communication, providing the person with a clear understanding of the nature of the project, your expectations, and the deadline.
“You have to make sure they’re willing and open to speak up, to let you know if they’re over-stressed or overloaded—what kind of bandwidth they really have. The biggest piece there is maintaining that transparency in both directions.”
That honesty about workload can be really hard to extract from certain individuals, especially someone who is very ambitious and wants to grow.
I think there are two major factors in goal-setting. One is making sure that the goals set a person up for success in the long run, both individually and for the team. For example, for a new Rep, the goals for the first couple of months are targeted towards getting them to hit that full quota. And second, is the individual buying into the goal?
From a sales perspective, there isn’t quite as much wiggle room in goal-setting. At the end of the day, the goal is for them to hit or exceed their quota. For sales support or account management, I’m monitoring customer retention, response rates to clients. What are their metrics? What will help the individual make sure that they’re hitting those goals and meeting those expectations?
“More broadly, where do they want to go in their career and how does that relate to the immediate goal? You need to create goals that will give them the opportunities that they care about as they look to grow within their role and move ahead in the company.”
It’s really dependent on both the buy-in from the team members, as well as the buy-in from leadership.
Expectations need to be aligned throughout the organization to make sure that we’re all on the same page and have the right action plan to achieve those goals.
“Making sure that goals are very clear and that everyone is unified in those efforts is crucial. If you’re not all working towards the same thing, you’re not going to get anywhere.”
When it comes to expectations, I am very clear and direct up front while I am looking to hire someone. I tell them clearly: this is what you will need to achieve.
“I make sure that anyone walking in the door has a clear understanding of what we’re going to be asking of them. Those expectations are repeated through the onboarding process and on an ongoing bases through use of individual and team metrics.”
We talk about team goals and company goals all the time. We want to make sure it’s at the top of the mind for everyone throughout their day, week, and month, and onward.
For my team specifically, I’m looking at lead to opportunity conversion. Earlier in the funnel, I am watching email metrics, for example, email reply rate compared to email volume. Then, from a close perspective, I’m watching the days duration in each stage, noting how long it’s taking for a deal to move throughout the pipeline.
“The two big buckets I’m looking at are the email lead combo and opportunity progression. You could call it weighted pipeline, the value of the deal times the percentage of the probability of the deal; so we have an idea of what’s going to hit and what we can project from there.”
I track them very similarly right now. For team metrics, I’m much more concerned with the overall opportunities, whereas, for an individual, I focus on the progression from a prospect to an opportunity to a closed deal.
“My approach to individual metrics is more granular, so I can get an idea of where people are hitting walls and where they might need assistance. For the team I’m looking at weighted pipeline, an aggregate and average of days in stage.”
The qualitative is always the harder to track.
Quantitative is much easier.
You can watch the numbers change, but it’s difficult to track the quality of the opportunities, the meetings that people are having.
Someone could have a pipeline that looks really awesome, but if they’re not quality, how do I identify that? I approach this through one-on-ones with my Reps where we discuss the quality of deals that are closer to the finish line.
“I find that if you’re asking people point blank about a specific deal, you get a much better sense of it, as opposed to just looking at a report in Salesforce.”
The quality of human interaction comes through in pipeline review, through team chatter, but it’s still difficult to track.
More tips to master managing intangibles.
“One of the important aspects of giving positive feedback is doing it on a regular basis, and in a visible way.”
When someone is doing really well or has positive indicators, I note that in a one-on-one, but also in a team setting, whether on the team Slack channel, a team meeting, or just in the morning, as everyone’s coming in and chatting about the day before. I publicly acknowledge that this person handled something really well or effectively addressed an area for improvement.
As opposed to sharing positive feedback with the group, I try to keep the strongest negative feedback to a one-on-one setting.
“If it’s not something drastic and I just need to comment on how they could have handled a situation better, I think it’s fine to bare that in a team or collaborative setting. Sometimes the whole team can benefit from witnessing the discussion.”
But, if it’s a performance-related issue or something inappropriate happened, that definitely needs to be handled in a private conversation. It varies with the situation.
It very much depends on the individual and the team, but in general, it’s important for myself and the individual to have a mutual understanding of where they want to go, what direction they’d like to take their career.
“Retention is really hard, and if people don’t feel they have room for growth or that they have the ability to develop and learn within the company, there’s always another job—especially for a strong performer. Keeping that talent, those high performers, within the company is the ultimate goal.”
I think it’s really important to have regular check-ins with people about their professional development–quarterly at a minimum–to get a pulse of what they’re looking to achieve and how they want to be progressing within their role and within their career.
As a startup, our team is constantly changing and growing, and it’s important for me to have an understanding of what different individuals are looking for as we grow. Are they happy to be an individual contributor and really just want to knock it out of the park, kill their quota? Or is it important to them to get peer coaching experience and eventually lead training on a regular basis? It varies, and you need to know so that you can provide the right guidance and opportunities for them to develop and grow.
I am a very metrics-driven manager, and our organization is strongly driven by metrics, so if someone is not hitting their performance goals, it’s a very clear and direct conversation.
“Every week, in their one-on-one, if they’re not hitting their goals, we’re talking about what they’re doing to fix the problem and why the fix hadn’t happened in the previous week. It’s very important to me that we have an open conversation, because if the problems aren’t corrected, there are going to be repercussions.”
Frankly, they’re not going to be on the team very long if they continue to not hit performance goals, so for everyone involved, it’s important to get ahead of that.
This is why I look at the different categories of performance metrics throughout the week and the month. If someone is low on the prospecting and engagement side–and so they aren’t converting enough leads–then their opportunity close the next month is probably going to be below par. So tracking those types of metrics, I hope we can make improvements before it becomes a problem. Instead of always looking back at the previous month, I want to look forward to plan how we can fix it for next week and next month.
On my teams, we generally have people doing parts of the job they want before they get the full promotion.
“For someone who’s in an individual contributor sales role and wants to move into a manager role, I’m looking to see if they’re already providing some of that coaching to newer people. Are they showing those qualities and taking some of those steps proactively? Are they demonstrating that they’re ready for a promotion?”
The other big piece is how they’re performing in their current role. Are they exceeding performance goals in the categories that they’ll need for their next role? It definitely depends on the role, because being an individual contributor on a sales team is very different from being a sales manager.
When someone is a morale problem or is no longer hitting their metrics goals, it’s time to have a conversation with them and probably manage them out.
Even if someone has done really well in the past, but they aren’t continuing to excel or to help the team improve collectively, then this isn’t the right place for them. Of course, they’ll have an opportunity to correct the issue.
“This is one of those situations in which you want to get ahead of the problem as quickly as you can—to identify a potential issue and catch it before it gets out of hand.”
But that’s not always something you can do.
The best way to address the issue is to have a direct conversation with the individual to identify what is missing.
“I want to understand why they’re disengaged. Is something putting them off? I really try to use the team culture, the team environment, to encourage people to stay engaged and driven—to
be excited to be a part of the team.”
We make sure everyone understands the sales environment, that if they’re not cutting it, they won’t have the job forever.
We use the reporting metrics and performance metrics to help people understand where they’re positioned relative to their own goals–but also within the team–to try to keep people engaged and moving forward.
Delegation and professional development is key. Depending on the person, there are different things that are going to keep them engaged. Some people want leadership opportunities. They want to help train new people, or host training sessions, or lead team meetings—to become a player/coach.
Other people like being an individual contributor. They like selling and chasing their numbers, but they’d also like some side projects, whether that’s working with someone else within the company, or thinking about new ways to prospect. Or maybe they want to
develop new tactics for moving deals forward, or for re-engaging potential customers who fell off earlier. It all goes back to professional development.
“You keep your star performer engaged by helping them find a balance between what they’re doing today and what they want to be doing in the future.”
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