3.7: How to Keep Sales Conversations Moving During a Busy Holiday Season (Kristin Moore)

Sammi Reinstein: Hey, this is Sammi Reinstein, and you're listening to Conversation Starters. On this show we talk all about bringing conversations back to B2B marketing and selling, because if there's one thing we know about doing business in the revenue era, it's that the best customer experience wins.

Elizabeth: Season three of Conversation Starters is brought to you by Really Good Sales Plays a landing page built to inspire your sales team, whether they're in- bounding, out- bounding, or managing a deal. These plays are proven to generate pipeline and close deals so you can celebrate more wins. Check them out at Drift. li/ salesplays. Now to the episode.

Sammi Reinstein: Let it snow, let it snow, let it snow.

Elizabeth: Oh, someone's in the mood for the holiday season.

Sammi Reinstein: Well, these days you can't go anywhere without hearing it, and people start celebrating the holiday so early now. In September, you're already celebrating Halloween, and then Halloween hits, and it's like Christmas.

Elizabeth: Yeah, everything's at least a month ahead.

Sammi Reinstein: It's at least a month ahead.

Elizabeth: If not more. But that's okay, I love the holiday season.

Sammi Reinstein: I love the holiday season.

Elizabeth: Do you have a favorite holiday?

Sammi Reinstein: Thanksgiving, for sure. For sure.

Elizabeth: I think Thanksgiving is an underrated holiday. I think it gets overlooked, but it's a great holiday.

Sammi Reinstein: It's a great holiday. What's not to like about it.

Elizabeth: And it kicks off the rest of the holiday season, if anything else.

Sammi Reinstein: And it's hands down the best food of all the holidays. I don't know why it doesn't get more attention.

Elizabeth: True. Although I will say, turkey is mediocre, but everything else around the turkey, phenominal.

Sammi Reinstein: Phenomenal pie.

Elizabeth: Oh yeah, obviously pie.

Sammi Reinstein: It's great.

Elizabeth: And the leftovers. Even a leftover turkey sandwich when you put like the cranberry, oh my gosh. Okay, I'm making myself hungry, so we need to move on. But on the note of holidays, very excited for today's episode, which is all about how to keep your sales team inspired, motivated during the holiday season, and also taking that to the conversations they're having with their prospects and customers.

Sammi Reinstein: Yes, absolutely. So today we invited Kristin Moore onto the podcast, who is the Head of SMB Sales Development at Motive. Motive is a platform that combines hardware with AI powered applications to connect and automate physical operations. And like Elizabeth said, Kristin's going to talk to us all about how to motivate your teams and how to keep hitting your numbers through the holiday season. Kristin, thank you so much for coming on Conversation Starters.

Kristin Moore: Thank you for having me.

Sammi Reinstein: Of course. So this season we have been breaking the ice in the beginning of the conversation, by asking what we would say a conversation starter, most people might call an icebreaker, but Kristin, we are going to talk all about the holiday season and how sales reps can prepare for the holiday season, and all of the out of offices and notifications that you get with that. So with that being said, my conversation starter for you is, do you have a favorite holiday or holiday tradition?

Kristin Moore: Oh, it's hard to choose one, but I would definitely say Halloween. One, because I used to love trick or treating. I mean, I would try to get as much candy as possible, but also now I have a daughter, and so thinking about the costumes I will put her in, and taking her trick or treating is just really, it's re- energized me around that holiday, definitely.

Sammi Reinstein: Yeah, it's funny, my brother who started his career as an SDR, we would put out all of our candy on the table and then he would barter and take, somehow I ended up with no candy, but me being now the marketer, I had all the best branded and cutest candy.

Kristin Moore: You see, it all works out. You see, it all out.

Sammi Reinstein: It just goes to show, it starts young.

Kristin Moore: Exactly. We all know our roles from birth, right?

Sammi Reinstein: Kristin, can you just give us a little bit of background on who you are and what you do at Motive?

Kristin Moore: Sure. Yes. So I've been with Motive for just about three years. We were originally called Keep Trucking, but we just went through a rebrand. And so during that time I've been in both AE and SCR management. Right now, I'm the Head of SMB SDR. We have a team of about 70, nine team leads. It's both inbound and outbound, very global team. So just had a ton of fun leading these teams and understanding the different things that come up in the small business space as well as inbound and outbound SDR.

Sammi Reinstein: So as we're wrapping up Q3 and we're heading into Q4, we talked about we're heading into a holiday season, and with a holiday season comes PTO and people who, maybe even people on your team who are going out of office who you thought were going to be able to hop on a call or whatever that may be. So, what are some things that your team is already thinking about?

Kristin Moore: Honestly, I always feel like Q4 sneaks up on us, no matter how far ahead we try to plan. But right now, we're thinking a lot around for the inbound teams, they're aligned with marketing forecasts. So we're thinking about who do we need in seat when throughout the holiday season, we're looking at historicals, what was volume actually like last year? Can we try to expect the same so that we can figure out how many people do we actually need their fielding inbound requests? Realistically, on inbound, we're going to respond to every inquiry, so a hot, warm lead. But we do know we can rely a little bit on our historical knowledge, reps that have been here for a while, so know they can split their shifts and things like that. In terms of outbound though, we're doing some hiring right now, so we're thinking about how to onboard people, considering times there might be out of office for not only the leaders myself, who knows. We're thinking about how to keep people motivated through the tougher holiday season, thinking about changing our messaging, how to plan activity. So is there a way that we can front load our efforts in October, early November, early December? Get people to hit quota so they can actually take some of that time off when people aren't responding. And we are also thinking about ways just to be more creative. I think during slower periods, whether or not it's the holidays or you're working in a seasonal business, you have to think about asking for referrals in times like this, find other lead sources if possible, re- engage old accounts, add additional touch points, All those kinds of things will just really help going into a season when we know realistically, end of November, end of December, we're going to take a hit. So, around those times.

Sammi Reinstein: Yeah, the creativity aspect too, I feel like when you go through those periods where stretched thin and you have to get really creative, sometimes those spark new ideas that you continue for the rest of the year, repurposing content, putting those into nurtures and all of those types of things when you're forced to think outside of the box, I feel like sometimes those spark the best ideas.

Kristin Moore: Completely. I actually think back to when I myself was an SDR, I think some of the best email messaging I wrote, was when I knew there was something going on in the world that I could reference to. So not only the value I could provide, I can't remember what year of Olympics back then, there was some year of Olympics I used a picture of you saying Bolt in one of my emails, and it got such a high response rate. So thinking about when it's around Halloween, is there a way, maybe it's not appropriate depending on what you're selling, but is there a way to pull that in? Is there a way to be a little bit more creative? People are probably paying attention to what day of the week it is. They know Thanksgiving is coming up, why not reference it in some way?

Sammi Reinstein: Yeah, we're all going through this very similar thing with the holidays, at least in the US side of things, if we're all doing Thanksgiving, or whatever that may be, that's a shared experience that you can nod towards in those emails. And maybe there's other relationship building things that you've done that you can include in that. Like if they're a skier, winter season's coming up.

Kristin Moore: Yeah, exactly.

Sammi Reinstein: Awesome. And it is also an interesting period of time, because coming up on end of year, on one hand there's a lot of people that have this budget that they have to get rid of, and on the other hand, there's holidays and PTO. So as a seller, you have to be mindful that there might be a prospect that you can nurture and have a great deal with, but at the same time being respectful that it is a holiday season. So how do you encourage your team to balance the number of touchpoints they make with a prospect while also being respectful that it's a bit of a chaotic time?

Kristin Moore: Totally, definitely. I think again, for inbound of course, we're likely not going to change that much, but back to your point of that collective experience, we may change the way we open a call or just building rapport on the call. And calling out, there's no reason to be robotic, so let's call out, like, do you have any plans? Maybe we're waiting to transfer a call, or who knows? Ask really quickly in that pause period, do you have any plans for the upcoming holiday? And just see if you can really build the rapport there. So for inbound, not much, but for outbound, of course, being a seller and in my head, knowing it takes so many touch points to reach someone, I hesitate to sort of change that overall number. I think it's more about being intentional about when we are doing those touch points. So, can we reschedule steps to another day, if it is right before the evening, before a holiday, can we schedule them around people's out of office? What are we saying on the phone? Are there emails that aren't performing as well we can maybe remove and replace with something else? And I think, as I mentioned before, can we just increase our productivity at different times in the month? So knowing that something is coming up, can we add 15% more in the beginning of the month and hit quota earlier? That's what I'm always going to continually try to drive the teams to think about. One concrete example is, our outbound teams have a goal of adding 15 new contacts to cadences a day. When you think about that 15% change, it's just two more contacts a day. So really giving people that tangible goal, explaining to them what doing a little bit more in the beginning of the month means, that will actually increase those dials and emails, but hopefully in the front of the month so that when we're talking about November and December especially, hopefully by then we're not having to work too much around the holiday. That's the goal.

Sammi Reinstein: Yeah, I think intentional is the golden nugget information there. You don't necessarily have to take away all of those touch points that you know are effective for your team, but just being more intentional about them, making sure you're adjusting the messaging, adjusting the time that those are being sent out. And I think that's a good rule of thumb for pretty much anyone in business around the holidays, is just being more intentional with your messaging.

Kristin Moore: Definitely, definitely.

Sammi Reinstein: Throughout your sales management, you mentioned that you have managed account executives and also SDRs and BDRs. Have you noticed an overall shift in priorities with prospects as they approach end of year?

Kristin Moore: Yes. I think this has really changed depending on the industry I've worked in though, or sold to. Some are a lot more seasonal than others, or some have different budgeting priorities at the end of the year than others. So, couple of years ago, I worked for an applicant tracking system, we're selling to talent teams, we're selling to recruiters, and in Q4 they're actually doing so much prep work and thinking about hiring in Q1, that actually doing and thinking about an implementation at that time was typically not something they could handle, so in terms of pulling the trigger at that time. So we were thinking a lot more about nurturing prospects during that time, scheduling meetings if we knew that they might be buying later than following year, things like that. I've also worked for third party delivery at Uber Eats. So depending on geography, restaurants are very affected by weather. People are also very affected by weather. They might want to stay in and order in the colder months. So it's actually a great time to call and get into restaurants. And then here at Motive, Q4 is often also busy, because certain industries that we serve, we do sell to a wide, wide, wide range of companies and businesses in the physical economy. But if you think of long haul trucking, for example, it might be peak season doing all these holiday deliveries, but maybe some other industries like construction, again, depending on where they are, it might be too cold to do some of those projects that they did earlier in the year. So, I think it really is so dependent on what company you're at, who you're selling to, what your product is, and that's something that as sales people, we need to be really tuned into to prepare for the end of year.

Sammi Reinstein: Yeah. Know your buyer, know their struggles, know their needs. I'm also curious, just as, you know, we see in the news pretty much every day, it's hard to scroll on LinkedIn without seeing things around budget cuts and hiring freezes and layoffs. And we know that teams right now, especially on sales teams, there's a big focus in efficiency and effectiveness, and especially around the holidays, I think that's where you see it come into play. How is your team, especially on the SDR team, thinking about efficiency right now?

Kristin Moore: In terms of efficiency, again, I think it goes back to that intentionality. We're thinking about, are there steps that we can remove? If there's something that we're just doing in a cadence, a call step or an email step that isn't getting results, can we remove it at this time? Can we increase our productivity in the beginning of the month? What can we do to use our resources at this time? We've done a lot of joint call blocks with AEs and SDRs. On the inbound side, we're thinking about capacity and. Can we push the SDR to do one more MQL a day, for example. So there's been a lot of things to just try to keep people efficient. I think it's also important as I think about this, to get commitments from people. And that's another great tool to increase efficiency during the holiday season, is beginning of the month with the reps on your team, ask them, what are you going to do this week? Realistically, do you have out of office? I don't want to be the person who's saying, you can't take this day off, but if you're taking an entire day off, how are you going to make those other four days of the week as efficient as possible? So it's about that intentionality and the commitment, getting a commitment from each person to drive their own outcome as well.

Sammi Reinstein: Yeah, and commitment also helps with visibility just for the rest of the team, like, what are you working on?

Kristin Moore: One hundred percent.

Sammi Reinstein: I also love the joint call block with the SDRs and AEs. I think that's a great way to get aligned and also drive accountability there. So what does communication between your SDRs and AEs look like to make sure that they know when each other will be out of office, and making sure that they're really in sync there?

Kristin Moore: Since we're SMB, we don't currently have territories or pods set up. We actually have automations that help us round robin to this large group. So when one SDR sets a meeting, they create an opportunity. We get an automatic assignment of the next AE in the round robin. But of course there are times when that falls through. Let's say that the AE has been kept in the round robin within our system, but they're actually out of office. So we created a buddy system that we built out. That way, and this is sort of agreed upon, and everyone's on the same page. If their AE is out of office, the buddy will take that opportunity for the foreseeable future, field any questions, take the meeting, follow up. And then of course, we utilize calendars a lot, make sure that we're checking the AEs calendar. We use scheduling tools within Salesloft to make sure we're suggesting the right times as much as possible. And then, especially on my outbound team, right now it's a smaller group, shared Slack channels where the AEs and the SDRs are expected to actually communicate about each meeting scheduled, give feedback publicly. It's not to micromanage, it's just to make sure that there's eyes on it and nothing falls through the cracks. Also, with those joint call blocks, I was just thinking, this goes back to the last question, but another way that those are really efficient is if you have somebody and you get them on the phone during a call block and your AE is right there, you guys could just go and do the discovery right there. There is no scheduling an additional meeting. So yeah, we just try as much as possible to have a good relationship with our AEs, break down barriers, or break down miscommunication, and make sure we're communicating literally either on call blocks, in Slack channels, through our scheduling tools, keeping our calendars updated, and keeping that commitment to each other.

Sammi Reinstein: Yeah, I think that's all great advice. And researching for this podcast, one of the things I noticed that a lot of people were giving you accolades for, was figuring out on your team what motivates them, and really using that to help them reach their goals. How do you use this skill to keep your team motivated as all of the holiday distractions start to pop up?

Kristin Moore: As a people leader since I started, one of the things I try to do immediately when I meet a new team member or join a new company, is understand why are they there? I mean, at the end of the day, there's a lot of fluffy and nice things we could say about why we work at companies, but ultimately you get a paycheck from it. And especially in sales, there is a variable portion of it that you can do with maybe as you please. And it's tied directly to metrics and outcomes. And so, I love to understand, hey, not to be too blunt or weird about it, but what do you do with your commission check? Why are you here? And there's been so many things along the years and even now, that I've learned about people, some people, it's purely promotion. They want to get to that next step. Some people, they're just extremely competitive. It's not about the money, but they want to beat the person sitting next to them. And so in one- on- ones I'll be like, hey, how are you pacing against blah, blah, blah person? I really try to keep one- on- ones very light and conversational with people so that I can get on that level with them. But then for those that are money motivated, there's so many things, down payment, sneakers, saving for a vacation, growing your family. There's so many things that you can directly tie to outcomes. And there's so many ways to remind that person of those outcomes when times are slow or things are going wrong. So in the holiday season, if somebody is just not hitting activity goals, let's say, I can easily point to that thing, like let's say they told me they want to hit 120% because they want to buy some designer purse, I can literally send them a picture of that purse and be like, how are we tracking towards this? Or ask in our one- on- one. And that's the level of connection and trust I really try to build with my team, because most people don't want to hear, hey, you're falling behind pace. They usually know that already. Our metrics are very visible, they usually know that. But sometimes if you're like, hey, where are you towards your personal goal? It helps them to take that ownership and really, really pick up the pace, or do the activities that they need to, to get there. And then it's also a way, if they just aren't motivated by it anymore, you can reevaluate too. At that stage, you can have a really open and transparent conversation about, hey, I don't see this as being your motivation anymore, help me help you figure out what that next thing is going to be, and let's work through this slow time. So highly recommend for any managers out there, do that before Q4 so that you can manage your team with just emojis and gifts through the holiday season.

Sammi Reinstein: I would love that if my manager sent me a plane ticket or added it to my pacing goals. But you're totally right. I know if I'm not hitting pacing, or whatever that may be, and it's far more motivating for someone to come back to me and be like, have your motivations changed? They're like, remember this trip you wanted to take? Where are we facing towards this? Yeah, I think that's really great advice. Well, Kristin, thank you so much for chatting with us. I think this should be mandatory listening for SDR leaders, especially heading into the holiday season. If people want to learn more about you or Motive, where can they find more information?

Kristin Moore: Yes, definitely. To learn more about me, I'm on LinkedIn, of course, Kristin Moore, SMB sales. You can learn more about Motive at gomotive. com. We are definitely hiring, also for sales roles, so if you're looking for a job, we've got them. And yeah, those are the main places.

Sammi Reinstein: Awesome. Thank you so much, Kristin.

Elizabeth: Sammy, the next time I lose motivation, please remind me that I am tracking towards a Colorado ski trip, and that will just get me right back up. I loved Kristin's methodology there. I don't know why I have not thought of it yet.

Sammi Reinstein: I honestly would love that added to my pacing. Like, here's ski tickets, you got to get there.

Elizabeth: Are you red, yellow, or green towards your goal?

Sammi Reinstein: Yes, towards your goal, yeah. I love that. I think Kristin did a really good job at explaining how she finds the what's in it for me, for her sales team and applies it towards this holiday season. It's so chaotic, there's so many distractions. And just refocusing towards those goals and those personal goals, I think is really effective.

Elizabeth: Yeah, and like you mentioned on the episode, I thought it was really valuable. Yes, motivating her own team, but then how can her SDRs take that approach and use it with their outreach and when they're having conversations with external prospects or customers.

Sammi Reinstein: Yeah, exactly. Taking the what's in it for me mentality towards your buyers as well.

Elizabeth: Yes. Well that is our second to last episode of this season, so make sure you tune in next week for our final episode of season three. And then, enjoy your holiday season.

Sammi Reinstein: Happy holidays.

Elizabeth: Jingle, jingle, jingle.

Sammi Reinstein: Jingle, jingle, jingle bells. Thanks so much for listening to Conversation Starters. If you like this episode, please leave us a six star review by clicking the link in the show notes, and hit subscribe so you never miss another one. You can connect with me on Twitter at Sammi Reinstein and follow all of our shows at Drift podcast.