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Director of Sales Operations: Anthony Conrad of Tapclicks

Anthony Conrad jumped onto Sales Operations Demystified to share his knowledge and experience in Sales Operations.

Check out all the other episodes of Sales Operations Demystified here.

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Tom: Hello and welcome to a very special re-recorded episode of the Sales-Op demystified podcast. Anthony and I recorded this a couple of weeks back. We had some technical issues but Anthony’s back, so this isn’t actually the first one. Anthony’s intro, I did a more professional intro- I think -in the first one we recorded. The last professional intro is that Anthony has a wealth of experience both in sales marketing and entrepreneurship, right?

Anthony: Absolutely.

Tom: This winding part has led him to become Director of Sales Operations at TapClicks. The t-shirt that you can see actually, if you’re listening on the podcast, you can’t see the t-shirt. On the t-shirt that Anthony is wearing says, “Meet me at the bar graph” and this apparently is TapClick’s motto. With that in mind, Anthony as a guest, welcome to the show.

Anthony: Thank you so much, Tom. It’s a great pleasure to be here again. Things happen and that’s the nature of [unintelligible 00:01:00] problem solving and coming up with great solutions.

Tom: Big [unintelligible 00:01:05] Thank you. More about TapClicks later. More about that motto later. My first question is, how did you actually get into sales operation from your extensive career in sales, marketing, and entrepreneurship?

Anthony: Sure. Honestly, I believe a lot of it was serendipitous. My first job working in a sailboat yard on the coast of North Carolina, I just took it as a summer job, and just figuring out how to be helpful in this job. Looking back now, I see a lot of operations foundation in it of ensuring inventories are properly planned, making sure that there is no slack in the system, making sure there we’re keeping everything on schedule and when things do hit the fan, keeping calm and figuring out, “Okay. What do we have? Where do we need to be and how do we get between there and here?”

I drew a lot of experience through other roles as well. Working in online payments, that’s at AT and CSM, just people management, looking at data and figuring how to tell the story. A lot of my journey has taken from there and when I was tasked with taking on the SMA and general sales operations at Tap, it was something that– When you have any business, especially one that’s in transition, acquiring systems, making technological migrations, you just need somebody who can take a step back and look at the forest, not just the trees. I think that that’s really what drove me to thriving in this role.

Tom: I think you just lifted off three things that I think describe sales operations really well. It’s people management, looking at data and telling a story.

Anthony: Absolutely.

Tom: Will you say they’re the three core skill sets that you need?

Anthony: 100%. I’m not a mathematician or engineer by any means but it’s objective thinking and not just being able to understand, but to be able to communicate, as well as something I use a lot in my sales team’s to even onboard them and get them up to speed is I use the analogy of, “You’re a doctor and then you’re a pharmacist.” When you’re a doctor, first you have to gain the trust of those around you, you have to establish your expertise, you have to understand the symptoms and then, prescribe and gain an ownership and get those around you to trust in the solution.

Sometimes you have to adjust your regiment but you have to be very detail-oriented, very organized, and being able to truly understand progress is incremental. It’s more of a sailboat than a race car. A lot of people look at these amazing companies and be like, “How do I get to that point?” You can’t get to that point if you don’t go through the journey.

Tom: Talking about the journey, you mentioned about having the opportunity to become Director of Sales operation at TapClicks. Did you come externally into the organization to become that or did you have a different role in the business first?

Anthony: Originally– Funny story, I was living in Bogota, Colombia for seven years. I met my wife while I was in the states. We made a decision because she’s a lawyer for the judicial branch down there, “I’m a businessman. I’ll go down there.” It kind of restarted my career and went through a different type of sales and career journey than most 26-year-olds would. I was in a position where I was tasked through an outsourced position as the personal assistant to the president of TapClicks.

It was a lot more than just calendar management and appointment setting because we were trying to build out our inside sales team and to have that kind of strategic management understanding, how do we design the product? As I had a human-centric design background. How do we understand taking the marketing to tell that story? How do we position that and develop it for these different networks and markets that we were looking at? After coming home to the States for the holidays, I saw family. I saw friends. I saw the opportunities. I was like, “You know, maybe it’s time to go home.”

I gave my notice and Colby, big shout out to my president, is literally the most genuinely nice person in the world, took the news kind of hard when he got notice of it, texted me, and was like, “Call me right away. Let’s talk. What’s going on?” He said, “What if I were to give you an internal opportunity with us? Keep working with us. Keep figuring out– Because you’re doing a really great job and we don’t want to lose you.” That was really something that– It really hit me as that value. In a lot of companies, sometimes people feel like a cog in a machine and it was something that seeing, “Hey, I am driving value.”

We both knew I was doing great managing operations, especially the Colombian team down there. They’re a critical part of our team for BDR and market research. Actually, going down for a few weeks, Sunday, to be on the ground and take stock of what’s going on. He asked me, “What would you like your title to be?” I said, “Something that reflects my skills and value but isn’t pretentious.” That’s how we came to Director of Sales Ops.

Tom: That’s how we got there. Okay. Let’s focus on TapClicks now. The current sales ops tech stack that you guys are using.

Anthony: It’s pretty streamlined in terms of what I use mostly day-to-day. I tend to be a little bit more fiscally conservative, especially when it comes to tech stacks. I know they can get bloated. I really look for a strong ROI, but also usability and are you going to, from day one, see value but as you get deeper and more advanced as a user, get more and more out of it? I would really attribute it to three main platforms that we use, which as most people, Salesforce, plugged into that is Outreach and also Chorus. I love the trifecta of the three because though they kind of take a little bit of tweaking, it’s not totally set out of the box.

That trifecta can give you the full 360-degree view of what is the actual kind information that you need, how do you engage them through emails, through different sequence steps of social interaction? I’m a big person for social selling. Chorus, from an enablement side in ops, it really is so intelligent and takes the pain out of coaching and ops management by noticing little tiny things of filler words, next steps planning. Are you kind of doing a weaker type of follow-up close, or are you setting the success steps in this call? Talk ratios are huge. The science behind who talks how much, depending on the call and interaction, it’s mind-blowing what can be done.

By balancing these three together, we’ve been able to build a kind of an ops culture. Not so much sales, but even just revenue operations. From the cradle to grave of what we call the sales bow tie rather than a funnel with the LTB factored in, with success backed by marketing. These three absolutely linked together and I get a lot of proposals and I love to having conversations and seeing what’s new, but right now this is my bread and butter go-to.

Tom: Awesome. You have the theorem, big [unintelligible 00:10:34], you have the sales enablement with outreach and then tracking all phone calls and everything with course?

Anthony: Exactly.

Tom: I like how you’ve kept that really simple. You’ve taken solid tools that do one thing really well and you’ve tied them together and now I assume you love improving their integration and improving how you use those tools.

Anthony: Exactly, and I got to give a shout-out to the teams that are account managers on each of them. They really, especially with Chorus and Outreach, they have this user-centric design, a great way of educating and enriching the use of it. I actually did get early access to the coaching platform of Chorus. Building a coaching culture is something that I’m really big on. Not just me to you as a rep, but building peer and individual culture for continuous improvement. They’ve already started building that in and I’m just so on fire with it.

Gone are the days of the boiler rooms, in my opinion, is just like pounding phones and just law of averages. It’s about really understanding who you’re talking to, how you speak to them and how you engage them with a little bit of personal flair and just genuine nature. I’m very notorious for saying, “If you wouldn’t read or engage with this, then nobody will.” Sometimes I get people who are like, “I don’t read anything.” I’m like, “Well, then maybe you shouldn’t be writing content.” [laughs]

I always love just being real and having a conversation. It’s amazing what conversations can do where proposals and white papers sometimes can do, but in reality, everybody is a human being. If you connect on that human level first which is driven by the data, I can pinpoint and what works, what doesn’t work. These three absolutely they deserve all the credit.

Tom: How are you dealing with data quality, specifically in Salesforce at the moment, especially with all this information coming from those two different tools?

Anthony: We actually went through a very hard type of quarter of merging sales forces. We had to different sales forces, we had so many different marketing research stats coming in of personal lists, [unintelligible 00:13:21] was one where were using in LinkedIn Navigator. All of these different sources. Everybody knows Salesforce doesn’t have a native deduping tool in it, that’s a metric data quality issue.

[unintelligible 00:13:36] scores depending on how you tweak it, it’s something where it’s about developing that kind of ops culture across the organization. Having regular, not just checkups and auditing, but really getting to the root of if this is a bell curve, what is 60% to 80% of our issues? Most of the time it’s very simple to pinpoint and minimize it and then once you master that and really drill it into the onboarding and the coaching culture for the data teams, then you can then focus in more and more and more home to get that scrubbing better. It’s about not siloing the organizations, it has to be a constant conversation about who is working where? What tools are working, what aren’t, and not to throw the baby out with the bathwater.

Tom: Got it. Salesforce not having a native deduping tool. Why do you think Salesforce haven’t built that?

Anthony: They have them in their marketplace which I think it’s worked out well financially for them. I think it’s a great business if you’re looking to develop that type of a culture of like, “Hey, this is Salesforce. It’s not a CRM, it’s more of an operating system in a way.” That’s okay for them but, honestly, for me as an end-user, I would pay absolutely a premium in the baseline price to just have that. Because that’s the one thing about the database is you have to have your key parameters and then a way to ensure that your database is properly maintained.

Every organization is different. Maybe you have multiple different lines of different deals and it’s okay to have the same information across certain ways but, eventually, there has to be an axis. It has to be a key-core parameter. Honestly, if I were the one doing the product design, if we could go back in time to the original Salesforce, I would have that as one of the foundations of the product itself.

It’s a native de-duping tool. If you want you can switch it off from plug in your own and maybe have your own way of doing it but, from my conversations– I was at Ramp in Boston, run by InsightSquared a few weeks ago and talking with everybody. That was their number one right is, “This is one thing that drives us all nuts.” That pain as an ops manager just shouts out to me.

Tom: Yes. Okay. Let’s switch from the theorem into looking at your reps. Four questions. What’s the size of the sales team? Is there more than just you and the sales operations team ratio?

Anthony: Absolutely. My partner in crime, honestly, is our director of sales enablement [unintelligible 00:17:06], major shout out to him. I have ideas and philosophies and he knows how to put it into structure and context, and writing out curriculum. I would be a great, just off-the-cuff type of professor to drive great conversations and find insights but he really knows how to translate this into standardized materials.

It’s not super sexy looking so he makes it look prettier and more structured in terms of the formatting. If there’s anybody that, from a data side, from a sales side, to build out curriculum, he’s definitely the one on that. I’m a little bit more on a creative side, in terms of that but a major shout out him for assisting with the sales ops. Roger Flores, who is managing our remote operations down in Columbia, and [unintelligible 00:18:07] from our Hyderabad office. These are my go-to people in terms of managing our operations.

Tom: Cool. How many BDRs, SMAs and AEs?

Anthony: We have 10 BDRs in Columbia. I believe 4 in Hyderabad, 1 in our office right now in Boston. We’re building out our US sales team and for SMAs we have 2 AEs right now working on the SMA side, 4 in the India office, and enterprise, I believe we have another 4 in total, working on 250 employees and larger.

Tom: Got it. As you’re rolling out to set a new tool, when you have that new access to coaching on course, maybe. How do you get these teams to want to do the new thing?

Anthony: It’s one of those things that I’ve been in so many orgs where they have the classical corporate sense of directors, executives, and VPs. We’re investing in it so now you have to be invested in it. I know the resistance. I was the resistant one. I was the one that’s like, “I hate this. I don’t want it.” Sometimes it works out that way. Anybody who’s used Facebook for years, I have since 2005. Any major change, everybody was resistant and then eventually they’d get over it. When you’re working with a sales organization, any downtime, any resistance, is lost revenue. What I tend to is, when I’m making these decisions, when I’m going through the trial, I run a true pilot study. I take key stakeholders from each different role and profile and get them in the room where I can get their impressions. I lead the training on it, how to use it, what are the tips, what are the tricks and take an objective poll of like, not do you like it but do you see yourself using this? Does this drive value? Does this solve a pain that you have? You have to be organized with this.

I made reference to human-centric design which is a beautiful design principle. I absolutely love using it because it has you go through a day in the life of the person you’re designing for, involve them in the design process and then doing constant contact to checkup and see, “Is this working? If you’re resisting it, why are you resisting it? Is it not working? Does it need to be tweaked?” That way you’re going to have a much lower churn-rate on your own technology. You’re going to have a lot greater investment from day one.

I think there are a lot of really great tools out there but I think sometimes being in the ivory tower, we make these decisions. It may be the right fit or it may not be the right fit because we didn’t have that initial conversation. It may be the flashy new tool on the road and maybe everybody’s doing it but if everybody is jumping off a bridge it may not be the right thing to do. You have to look at your org, you have to take the time. It’s like the analogy of you’re saving pennies to spend a dollar. I absolutely prefer to take a few hours, sit down, go through a design process with my team, get their investment and excitement and feeling over this rather than to shove something out and then make it fit.

Tom: Got it. Shifting quite slightly, when you have, you mentioned you’re heavily hiring in the US and you’re getting the US team, do you already have a process in place for onboarding these new salespeople?

Anthony: Absolutely, absolutely. Obviously, everybody kind of eats through their first six months in sales. I’ve gone through it so many times and it’s not just culture that you have to adapt to, it’s going into what is the actual sales process like for this org or this product or this industry? How do you get used to the tools? How do you get used to what you are selling in product knowledge and ramping that up? Even more so, how do you establish that, “Hey, I don’t just represent this company, I’m here to solve a problem for you”, and establish that?

It’s a process of product-knowledge, company-knowledge, market understanding, teaching them how to establish their own personal brand and to really get them off the ground with that. I always have this idea in the first few months, obviously, I can’t do this with everybody every single day, but in those initial frustrating days of being in a new role, I have two questions that I always ask my new reps, “Did you have a good day and did you learn something?”

Just drilling that in you establish the habit of them of, “Hey, I have an open door to give a gripe. If I had an issue we can talk about it right here, right now.” If they’re constantly learning something new and repeating it back, they’re more likely to retain that knowledge rather than, “Here you go, here’s a phone, here’s a computer, go sell and in three months I’ll talk to you and see what’s up.”

You have to crawl, walk, run in an organization and in those early stages that type of onboarding culture that’s standardized but personalized, I find that even when you are in the hiring process you have to look for candidates who not just have a rockstar performance but also coachability and is this person going to be on-boarded quickly? That runway is going to be there but anyway that you can standardize, shorten, get the investment and excitement of that person while the iron is hot, absolutely take it.

Tom: Good, so the two questions, did you have a good day and what did you learn today?

Anthony: Exactly.

Tom: Got it, because that’s just going to be reinforcing, I guess, positivity. They look for positive things to say, then also they’re learning because that will come back to you.

Anthony: Exactly and also it helps cut down on burnout too. That’s the one thing that I for so long in my sales career, especially when I was at CSM, I don’t have much hair to lose but I did lose a lot just thinking about work after hours and it’s my way of telling them, “Hey, it’s okay to switch off now. It’s okay to not be thinking of this. Recharge, rest, live your life outside and then come back.” That’s our close in that way. Then you do like a morning stand up, get ready and be able to do that.

I want my people to retain and recharge with what they know, but I also want them to be able to switch off and not have that anxiety of, “Oh I didn’t hit my demo quarter today.”

That’s yesterday, let’s focus on you enjoying your time and getting back and learning from it. Not throwing it out. That was yesterday, this is today and kind of like I was watching this morning the ICC semis of India and New Zealand. Every [unintelligible 00:26:51] bat is another red bat. If you’ve got a deficit just perform more at the end.

Tom: Now it’s a new day, you’ve had your stand up, you have this fresh sales team in the helm, and thinking about what [unintelligible 00:27:04], how are you going to be making them more productive during the day?

Anthony: Sure. Productivity is for me not nitpicking on what’s wrong. It’s positioning of, “Here’s an opportunity of where we could go better,” and then capping it off with the good news at the end. “Hey, this is where you’re improving, your handling times are down, your engagement is up, the sequences are getting more attraction than this.” I don’t take the good news/bad news cycle. I try to flip that because it’s one thing to have like, “Okay I’ve got the good news,” but you know the bad news is coming. It brings the sales out and a lot of times in sales words, it’s all about like are you a Rockstar or are you not. I’ve seen so many good reps quit because they just felt like they weren’t cutting it.

Everybody has times where maybe the road map is a little longer, maybe your funnel’s not so productive, but if I hear you have a really awesome call, I’ll go ahead and just send them a little slack message or pull them aside and say, “Hey, I just for this one specific thing, you did really well and I just wanted to let you know how grateful I am to have you on the team.” I’ve seen in a complete turnaround from reps that were just about to quit into top-performing reps, just because of that little thing. It’s not all commissions, it’s not all presents, clubs and trips. It’s about this day to day conversations.

When you do have to have, “Hey, this is something we can improve,” they’re more likely to listen to you if you’re not just a negative Nancy.

Tom: I think that that slack message sounds brilliant, “Really grateful to have you on the team.” I can imagine that having a really really good impact.

Anthony: I even do it sometimes, actually, sorry. If I know somebody is a little bit more introverted or not wanting to be called out, good or bad, I’ll just take a little Post-it with a sharpie and put it under their coffee mug and just write a little note like that. I literally have one of my reps, a few days later finally noticed that [unintelligible 00:29:43] and just picked it up and just gave me a nod. I had so many people who helped me along the way. It’s just that kind of paying it forward that I love and it really drives performance in the team.

Tom: Okay. Shifting on to KPI’s, how are you currently measuring or tracking the progress of your reps?

Anthony: First and foremost, I wouldn’t be a good rep or a sales op manager if I wasn’t looking at MRR and the almighty revenue in gross profit but we also look at the total lifetime value. Where are we positioning in terms of negotiation? Are we going for the kill, top-level revenue that’s most likely to turn or are we kind of going a little bit too low just to get the close? What is the life cycle of the MQL to close? How are we handling this? How many leads are just going stale?

I even had one a few days ago where I was just doing a preliminary conversation, the guy wanted a demo with me and he sent over some questions about the organization and I haven’t even had a conversation. I’m not going to show all my cards right away. I want to see, maybe this is worth it and I’ll open up. If I see value, I’ll be transparent as possible. Because I didn’t send over the information, he just canceled the demo. It’s like “It’s not worth my time.” I was just like, “Really?” It’s about as much them getting to know you as you getting to know them.

What I really strive with my team is when is a no a not now and knowing how to do that, knowing how to reengage it, knowing how to use proper technology in terms of that. In terms of, if you have a lead that you think is going to go stale but you set a calendar event 60 days in the future, that drives me more value as a manager than it does to just be like, “Okay. Junk. Junk. Junk.” I don’t believe in junk. Maybe it was absolutely like test, test at That’s okay. That’s junk but if they’re saying, “Well we use Zoom instead of UberConference,” that’s not a junk. That’s a not now.

It’s a time to put your consultants’ cap on and stay in touch and see, “Hey. What do you like? What do you not like? What what you like to see that you’re not seeing right now?” Activities are something that we look at heavily too and a lot of sequences. I see people, even using Outreach, they just use emails. This is the social age. The way that you get into peoples minds is not through their inbox. I’m a very power social user, tagging people in an article, knowledge sharing, commenting, interacting, even just a profile view. People are vain. They like vanity stats and, “Hey, who looked at you?” “Oh, whoa. It’s Tom. I haven’t talked to him in forever.”

That also builds the referrals as well which is another important track that I look at is how does the reps personal branding and management of the account drive the value? Referrals are honestly the cheapest, cheapest form of marketing possible but most people don’t realize who is unhappy or who is super excited unless we send out like some survey but you can see it in the data. You can see it in how many clicks they take, how many opens they do whether when you look at their profile or they look at yours. It’s all about these subtle communication steps that when you work this into your activities, it will definitely drive the dollar down a lot more.

Also, in terms of KPI’s, I’ve even started implementing in our team coaching culture of not just my scoring of you in your abilities but how do you score yourself? How do you score your peers? Developing kind of contests that build on that and incentivize it but at the end of the day, it is going to be driving those metrics that I want to see.

Tom: Pretty comprehensive, so metrics. If you had to choose one to measure sales rep performance, which would you choose?

Anthony: I’d have to honestly say– I have to say leads conversion more than anything. I don’t care how many steps it takes to close a lead. If you get a lead, I want you to follow up until they say, “Don’t speak to me ever again.” It’s about not being aggressive but more assertive. That’s something I have to really drive into people, is there’s a delicate balance between the two, but if you’re actively listening, you can turn a pipeline that you would put as 50% junk, probably down to 25 to 10 if you do the right follow-up on that.

That would be probably my favorite of all is, “How many am I giving you? How many are you making yourself? How many are you eventually converting?” Whether it’s 60, 90 enterprise sales. It’s six to 12 months. People get frustrated in three. It’s all about pipeline management. That’s my biggest KPI.

Tom: Finally, I know there’s a couple of people you want to shout out here. For the audience, Anthony actually has his own podcast which has quite an interesting concept. The question is, who has inspired you or taught most about sales ops but also sales marketing because I know you have a background there?

Anthony: Jeez, there’s so many of them, Jon Buchan of Charm Offensive, obviously, is one of my favorites in terms of creative marketing emails. He’s an absolute rockstar, wrote a drunken email, woke up the next morning, read it, thought, “Hey, this is pretty good.” send it to 20 to 30 of the top brands in the world and made CMOs laugh and now runs his consultancy, teaching others how to do it. Rockstar guy, just launched his own podcast.

Gary Vaynerchuk honestly, huge fan of Gary V. I know some people see him as a self-promoting person but he’s actually quite humble, and has taught me a lot about humility and hard work and empathy, and really understanding how to truly communicate, how to demonstrate your value, how to really engage with clients and understand, maybe it’s not what you’re selling but what you can deliver to them is the biggest issue.

Satish Bala, my latest guest on the podcast, a lifelong serial entrepreneur marketer, crazy, crazy life story himself, and doing his own consultancy, and now doing public speaking, was just down in Sao Paolo. A long-time friend of mine, absolutely love him. Actually, I mentioned Ramp Boston, Fred Shilmover, of InsightSquared delivered a keynote address at the event. He literally, not only from an op side but even as a hip hop head really just touched me with drawing in a pop-culture reference to explain the sales ops.

He quoted a Wu-Tang Clan’s Slow Blues, with, “Life’s ill, don’t get it pretzeled. I can’t show you, but I’ll leave a stencil. I’m talking about what matters, not figures. I’m pointing at the moon, and you’re looking at my finger” I was blown away because that is in essence, sales ops, is getting people to look at what really matters, and not just, “Oh, I’m in marketing. I want to look at MQLs and did we get– How many engagements did we get.” What is the real story here? Are we having lower engagement but higher conversions? Are we having higher conversions but lowe LTV? It’s all about the holistic understanding and somebody who understands sales ops but also the power of lyrics and poetry.

Fred is definitely somebody who– If I had a choice of somebody to have a beer or lunch with when I’m in downtown Boston, he’d be definitely the guy to hit up.

Tom: It would be Fred. I’m going to try and find that keynote as possible online and will link it below.

Anthony: Sure.

Tom: Awesome. Anthony, as always when we chat, I have a whole realm of different saying/lessons. Here are my favorite, the three– The way you summed up Sales ops almost off-the-cuff, people management looking at the agent and telling a story that was incredible. About your fellow organization or even your business being a sailboat and having incremental improvements rather than a race car. Then here, I’ve never heard this before when trying to get buy-in for a process or a tool that any resistance you’re going to get is essentially lost revenue.

Any changes you make in sales ops really need to understand or minimize the resistance you’re going to get from the team because they have literally people not selling developing business. There we go, Anthony. Any other general you think I missed apart from the wu-tang clan lyrics?

Anthony: Honestly, not off the top of my head but it’s absolute pleasure to speak with you, Tom. Thank you for giving me the opportunity and being able to speak about my passion.

Tom: Anthony, thank you so much again.

Anthony: Thank you.

[00:41:02] [END OF AUDIO]


Anthony Conrad of Tapclicks

Anthony Conrad of Tapclicks