Modern Performance Deep Dive: Dhiraj Singh, Inside Sales and Operations Manager at MemSQL
Over the past several years, Dhiraj Singh (Linkedin, Twitter) has seen the sales process from nearly all levels. Dhiraj experienced the perspective of a co-founder with OneCal, a social calendaring start-up. Afterwards, he worked his way up from SDR to AE and eventually Head of Sales & Marketing Operations at his last company, TechValidate. Dhiraj now serves as Inside Sales and Operations Manager at a top operational data warehouse MemSQL. There he uses his experience to manage a team of SDRs and account executives. Dhiraj has considerable amounts of experience running efficient teams and scaling them quickly. In this interview, Dhiraj reveals some of the wisdom he has gleaned throughout his career. On hiring, Dhiraj addresses how to determine a candidate’s prospecting ability during the interview and how to hire those capable of managing ambiguous situations. Singh shares his perspective of onboarding as a full team endeavor and on key onboarding benchmarks. From communication and culture, to goal setting and feedback, Dhiraj shares many secrets of the trade and what it really means to run an effective sales development team.
What’s the secret to hiring for high performance? What are the most important characteristics you look for?
We look for a lot of characteristics, mainly communication skills. I look for people to listen well and ask good questions based on what they heard from me, paraphrase what I said, and repeat things that I said. These are all things that show someone would be able to handle themselves on a good qualification call and really understand the prospect.
I want people who are hungry. I look at progression in whatever roles they were in and look for people who show they weren’t satisfied with the status quo in their previous positions. When they see a challenge, they actually enjoy coming up with solutions. They’re not the kind of person who wants to see the same issue come up twice.
I think that’s super important, especially for startups. The last thing is you need people who can deal with unstructured process and with ambiguity. We call one of our interview sections “dealing with ambiguity” and look for anecdotal ways that, when faced with challenges, they don’t get shut down but find ways to push forward.
I role play with candidates before hiring them. I don’t need them to understand MemSQL or our product, but I do expect them to understand whatever company they’re selling to. I want them to give me the role of someone they might sell to with as much context as I would need to have an intelligent conversation with them. I want to see how they ask questions and vet me. It’s really valuable to see what natural skills people already have and what they need to learn. Other than that, I’ll ask them about problems or issues they’ve faced in their career. Or if they’re fresh out of college, I’ll ask about big problems or issues they faced in clubs and have them walk me through step-by-step how they dealt with it. I want see that they figured out a creative solution, that they implemented it or communicated with the right people to make something happen that improved the situation.
One thing that’s really helpful is to make sure everyone on our team is involved in the hiring process. They are all part of the interview process and everyone gets a chance to do an interview. They take part in roundtables and deciding new hires. We have really thoughtful discussions about candidates so when anyone new comes on board, everyone has taken a little bit of ownership for new members of the team.
“I rely on my teammates to assist in the onboarding process. They help teach and are there to answer questions. It builds a really, really collaborative kind of onboarding for everyone.”
For my role in onboarding, I think the most important thing is setting very clear benchmarks, in what I expect from someone in their first week, in their second week, in their third week, and in their fourth week. I have that written down as something that we refer to every week during the onboarding process. Then there’s just a lot of open communication during that time, especially in the first month, where we check in every morning and at the end of the day, even just for five minutes, to make sure that I can answer questions and to make sure people have the right resources. It’s really just making sure that at no point during the onboarding process do they ever feel lost.
We’re a First Round company and our CEO is a really big fan of radical candor. When adding a new team member, the first day we talk about company values and how we see them. We talk about how we have radical candor, which means that in one-on-ones and in team meetings, we’re very upfront. If there are setbacks in any way, we talk about them. If you have feedback for people, we show them the charts. We explain those values and map them out so people understand what that looks like in our communication style. Our team is very product- and engineering-centric, so we talk about how that affects the company as a whole, so everyone is very operationally minded. Even the salespeople become pretty technical. It’s a difficult product, so we talk about learning the product and being able to confidently speak to the product. That’s part of the culture. We expect everyone to understand MemSQL and the database landscape to a certain degree. The last thing is we talk about unique things on our team. We thrive on everyone being very collaborative around knowledge and best practices and taking ownership of our new hires. It’s in a lot of parts of our organization, but we talk about it as something that’s unique to inside sales and how we want to keep that culture going so we can bring the best out of every individual member. It’s just a lot of reinforcement after that.
I’m constantly making small adjustments as I learn more and more about what I think makes a good one-on-one. For instance, I’ve come to believe that one-on-ones should not include metrics. We have metrics overviews and we do different kinds of team meetings and stand ups, so during one-on-ones we talk about issues that are better suited for that type of situation. We talk about what challenges they’re facing and I don’t mind digging in and bringing things up where we can work together to find a solution or remove a barrier. A lot of things that come up during one-on-ones are less about people hitting their metrics. What ends up coming up is more around, “Where do I want to be in two years, three years, and how do I actually work now to make myself ready then?”
“The more interesting part of one-on-ones is talking about development. What we end up focusing on is how a can person can develop professionally or build qualitative skill sets they might need to work on.”
When you’re in sales someone can know the product pretty well and really thrive at KPIs and metrics, but it’s such a different job than being an account executive, which requires a very different kind of skill set. In one on ones, usually we’ll talk about those skills and see if there’s any place where people feel that they have weaknesses and then talk about how they can improve in those areas.
Team meetings are pretty standardized. We go over the metrics for the team over the week, over the quarter, talk about any major standouts or shortfalls. Then each person on the team has a couple of minutes to cover their own personal what worked in sales last week and what their general plan is for this coming week. We have weekly meetings on Mondays and then every other day we have a 10-minute meeting from 3:50 to 4:00 where people walk in and write their KPIs on the whiteboard, any major events of note, and then we review it as a team. The only purpose is to promote accountability, so people expect that this is part of their day and share best practices, and it becomes another way to promote sharing of knowledge.
Performance metrics don’t play a big role unless there’s a major standout or shortfall in what’s expected. If someone’s approaching the end of the month and they’ve only created two opportunities instead of the seven we expect, then I’ll bring it up and we’ll talk about it and see what the plan is to get to goal by the end of the month, as well as how I can help. If everything seems in line, I’ll just check the data before one-on-ones to see if anything looks off. Otherwise, we talk about other topics.
First of all, it’s part of the hiring process. We hire good communicators and we’re very upfront about how communication is good for our team. Everyone joins the team knowing this is going to be a competitive environment and talking about what’s working is really important for the team. Other than that, we do a couple of other things. There are standups that help everyone communicate with each other. There are call blitzes where people sit in a room and make cold calls with each other, listening in and learn from each other. We have a team Slack channel where everyone communicates regularly. Then there are bigger meetings, like our weekly best practices meeting with the wider sales team where everyone gets a chance to talk about what worked well in lead generation and pipeline generation for their territory. Otherwise it’s all about hiring and culture.
It’s important they don’t treat the job as just a chore, but something that’s interesting and stimulating and that leads to them actually discussing their work lives and their strategies and tactics with each other.
I use all those same channels I just mentioned, plus physically I sit in the middle of the team. I try to make myself very open and approachable. If anyone Slacks or emails me, responding within 10 seconds is good. It gives everyone the feeling and reassurance that if they reach out to me, it’s a priority for me to respond and alleviate a concern or answer a question. The last thing I want to do is be a a bottleneck for their productivity, so I think that’s important. I think communicating goes both ways, so in one-on-ones I leave a couple minutes at the end to ask for direct feedback. A lot of people have thoughts that I actively try to incorporate. If a person mentions something that could be better for the wider team, I want them to give that feedback and have them see it in action.
Delegation is probably something I need to work on more. I always feel like I need to do something, rather than delegate it. When something comes along that needs to be done, I sometimes just do it myself because I just want it to be done quickly.
You should delegate the tasks that you want to do, that you would enjoy or think are really intellectually stimulating and are motivated to do.
I think about that a lot whenever there’s a team project where we’re trying to do something for the benefit of all our teams. I find it’s super valuable to get people to take part when they’re already passionate about a topic.
I try to delegate the things that I actually think would be intellectually stimulating to teammates because they’ll appreciate doing those things. I try not to delegate tasks I don’t want to do because they’ll resent you for that. That’s not a positive course of action. My secret is that any time that I’m doing something that’s going to affect the whole team, I try to get people on our team to take responsibility for it. For instance, my teammate Ryan is a big skier, and based on his idea we decided to do an offsite to Tahoe, which got approved and he was more than excited to plan. That may not help his professional career, but he really wanted to do it and I wanted to, too, because it sounded like fun.
I like people to set their own goals. I think the most important part is understanding how they came to that conclusion, how they set that goal, and how they are thinking. That way, I get a temperature check on how ambitious or realistic or maybe not ambitious their personal goals are. If it is metrics-related, we’ll put them up on the whiteboard during standups. It’s okay if people’s goals are different. In sales, there are very different strategies for email, for instance. There are a number of factors, like how personalized an email is going to be or how targeted of an approach someone is taking.
So it’s okay if goals are different as long as you’re striving to maximize the end result — meetings booked, opportunities created, and actual revenue being generated. Setting their own goals allows people to have the most amount of accountability and ownership for their own goals.
Teams are more data-driven in the sense that we back into the goal through historical data. It’s really just explaining why the goal is what it is and showing people step-by-step how we got to the conclusion that this should be the goal so people feel ownership. It sucks when there’s a big black box and no one really understands how we got there, especially for millennials. They want to feel like they’re making an impact and to have transparency. Even if it’s completely unrelated to their jobs, they want to know, “Why is this decision being made?” I make it very clear to my team why so they can ask questions or question it. So team goals are data driven but we’re just very clear on what the data is that led to that goal.
I think the secret is making it very, very clear why the goal is what it is. The other part of it is really broadcasting it. We use a tool called Ambition, which shows people exactly what their personal goals are and what their path is to that goal. Our Salesforce dashboard shows what the goal is going forward and it’s very visible. We have TVs in our office that broadcast certain goals and all the different KPIs that we’re trying to hit.
The more visible a goal is, the more people feel it is really important. The more they feel it’s really important, the more they’ll embrace the goal as their own.
We use the standard Salesforce reporting and we use a gamification tool called Ambition. We use other tools just to make sure we’re getting all of the data. We use People ai to get all email and calendared meeting data, so we have trust in the data integrity. Data is great — knowing all the emails being sent, all the meetings being booked — but there are now some tools that take the data and actually give you prescriptive analytics. Those tools make my life easy because I don’t have to analyze data, and they will continue to get better. It tells you how to analyze it and then I can talk to someone about a big shortfall or a big standout in their metrics. Those same tools are getting to the point where they’re more user facing, so before I even have to go to anyone, they’ve gotten the same alert.
For individual metrics, the first thing I’ll look at is the end result. For us that’s how many qualified opportunities are being created. From there I’ll go down to the basic unit of how many emails are being sent and calls being done. On our team, I really let people drive their own strategies, so it’s hard to look at volume. A lot of the time, I have to look at percentage and volume, so how many emails being sent combined with the reply rate they’re getting. Luckily, we have tools that can tell us the absolute numbers on replies and connects so I can see how many times a person is actually having a conversation with another person on the line or someone who replied to an email. The most important team metric would again be the end goal first, which is opportunities created. The next metric is actual meetings booked and completed. The third one is how many interactions, that is, actual email replies or phone call connects. That is the conversion path I look at.
The hardest thing is not necessarily metrics, but quality. My team used to be compensated on meetings completed. If they were with the right people and the right companies, that was what they were paid on. We changed that to qualified opportunities, which means not just that there needs to be a meeting, but it needs to be with the right person and a valid company, and there also is a need for our product and some kind of urgency that would make them actually get into a sales cycle with us and that could close within six to 12 months should it become an opportunity. The hardest metric to track would be how to bucket these meetings from good quality to poor quality. That can be tough because quality of meetings is going to become less important. Figuring out patterns across meetings and what’s actually working in the way people are setting them up, the actual tactics in terms of emailing and calling and how that leads to better quality versus lower quality meetings, that’s going to be the mystery. The thing we need to solve is how we figure out who’s getting better-quality meetings, because that’s how we spread best practices across the team. If we could metric that and track that well, that would be great. To do that, we’re applying more subjective fields that are filled out as meeting notes and driving patterns and ideas from there, but it’s not a science yet for us.
What are the aspects of qualitative performance that you like to pay attention to and are hard to instrument?
If there is one qualitative performance metric from my team that’s difficult to measure, it’s progress in their product and industry knowledge. It’s not a metric for current performance, but future performance. The goal is to get these people into closing roles. The day to day in an SDR role is not really that close to the day to day of an AE role, so one of the things I look for in people to promote is progressing in subjective skill sets like questioning skills, qualification skills, understanding the product and industry well enough to communicate confidently about that.
I use some prescriptive analytics tools for anomaly detection on KPIs that help a lot. I can look at a glance and get email alerts that tell me there is an opportunity for coaching in the next sales development meeting. There are other opportunities where you shadow people and during qualification calls to give really valuable live feedback about their questioning skills and qualification skills. That will become super important in their role progression.
I don’t know if there’s a secret.
One thing I’ve learned is that it doesn’t make sense to give positive feedback when someone is really just doing their job.
When people are doing well, I like to tell them and reassure them and make them feel good about things, but the issue is giving positive feedback when someone is just hitting their metrics. I try to avoid that because it dilutes feedback when people are actually going above and beyond. I think the secret is to give positive feedback scarcely, when it’s really deserved so that it means something. Otherwise, it’s just going to bite you in the ass because people expect things and when they don’t get them, it’s a disappointment.
It can be a little bit uncomfortable for some people. For me, I knew it was a challenge I needed to overcome. For negative feedback, it’s really important to have very objective evidence and not have it be something that isn’t measurable. You have to avoid emotions and really stick to what happened, even if it’s not metrics-based. If it’s a morale thing or a people thing, you have to bring up actual times when they negatively affected a teammate and have real events to back it up. Then you ask questions to the person to understand their mindset and not be dismissive.
I don’t want to tell people what they should be doing to alleviate a problem, I want them to figure it out on their own. Once they understand the negative feedback, they can come to their own conclusions and come up with a solution.
How do you do feedback where the answer is measurable (“fewer bugs in the code please”) versus less measurable (“You come off as aggressive, Pete.”)?
With measurable feedback, it’s much easier. You can just put things on the dashboard. When it’s less measurable, there still needs to be something objective. For example, one time I hired a consultant to come in and do a training session for my team on qualification calls and asking good questions. We had one person who was very skeptical and gave feedback on every topic the trainer brought up, to the point where it was being very disruptive. I pulled him aside immediately — and I think that’s also important to do it as soon as you see an event because then it’s really fresh. I told him his behavior was affecting his teammates and their ability to learn in the session, that he was talking for a third of the session and preventing the team from getting valuable time to learn. You have to make it objective, you have to make sure it’s not an attack or criticism of someone, and you have to really make it actionable.
All of the people I manage are between 23 and 30, so they’re all concerned with professional development and want to see a very clear path to their next role. I think the best way to manage it is to speak about professional development very regularly, bring it up during one-on-ones, and be transparent. The fact that it’s being spoken about openly at a regular cadence will keep it from ever building to a point where people feel like they’re getting a lack of professional development. It’s super important because no one sees a beginning sales role as a be-all, end-all. They have to feel like there’s a path forward and that they’re learning and growing.
First off, I think the people who are ready are doing really well in their day-to-day job. They’re performing well enough that they’re grabbing more responsibility outside of what would be their normal scope of work. They’re consistently taking more responsibility that’s closer to the scope of a future role and they’re doing it well. They’ve shown mastery in their day-to-day and have the time and attention to do more. Then there has to be a promotion available and it has to be the right promotion. Sometimes you have to work hard and create roles for people. If you think they’re valuable, you know it is table stakes for them to stick around and it’s worth it to create a role where they’ll add even more value to the company.
First, I do a check on engagement. We’ve done a good job in the hiring process, and usually I’m pretty confident they’re capable. It’s not that they lack smarts or skill set. Most of the time, it’s a lack of engagement or there’s a serious people problem, so I have to see if there are any issues with other people they’r accountable to. Then, as with any other negative feedback, you have to come prepared with very clear data so if you’re speaking about concerns of their performance, you have it backed up with very clear KPIs and metrics. You really need to get them to agree and own up to it. After that you can find a solution by getting their ideas. The last thing is you should be positive that they can could actually succeed by following the plan, but also be very clear about any consequence that could come if they continue a negative pattern or poor metrics. You have to be extremely clear so that, if you ever have to let them go, it shouldn’t be a complete surprise.
I haven’t had to deal with that, but if that situation occurred I would treat it just like giving negative feedback or dealing with someone who is causing a moral problem. It would have to affect other teammates in a negative way that affects their performance or future prospects. Then you would have to outline objective things and explain it to them in a way that motivates them and aligns things with their future growth.
First I would show how they’re affecting other people. I think it’s always good to show as much objective evidence first and then, after that, really just ask questions, talk about what might be going on, and show the difference between April versus November and how things dropped off. Then ask them to explain in their own words like, “What do you think could have affected this?” Then you have something to go off of to help alleviate some concerns or find a solution. If not, then you just need to outline very clear consequences and align it to their future growth and goals.
I’ve dealt with this a lot and I think there are always opportunities to do more. There are a lot of people on my team who we hire and they figure out how to perform really well as an SDR. Immediately, they’re thinking about how to make a bigger impact. The challenge is aligning that with their future, so I create new projects that will help that person grow professionally or monetarily. Align it with potential new promotions, create things that are both interesting and help them learn or make some sort of visible impact. There are always new opportunities to engage really star performers if you’re afraid of burnout or you’re afraid of boredom. It just takes a little bit of creativity and making sure that any new projects you create are not busy work, but something that aligns with their own growth or the company’s growth in some way.
I’m totally fine having conversations with people about not staying at the company if they’re not driven. I’m not too worried about attrition. Luckily we haven’t really had any on this team except for one person I had to let go, but I’m not afraid of those conversations. I like to be very open and I want to make sure we dig in and figure out what the motivation problem is, whether it has something to do with money or if it’s a people problem. I just ask my teammates to be transparent with me about how they’re feeling. A lot of times salespeople are motivated by money and compensation is really the main driver. Sometimes you just have to look at your compensation structure and make sure it’s aligned to the kind of activities and results you’re going for. Sometimes it’s out of sync and people are confused. The goal is to never have people frustrated by internal stuff like comp. It should be absolutely aligned and if it isn’t, it just distracts them from the job and you get worse performance. People are spending their time doubting or thinking about things that just are not related to selling and performing. It’s usually one of those things.
That is a good profile to work with because it’s kind of amusing but I think it that can be frustrating. You have to give people some self-development work on things you’ve identified that they need to improve on. It’s the art of helping people realize their own weaknesses and it’s not easy. I like to give people tasks or self-development projects that align well to what they want to do in the future, but through that they’ll realize they need some help. You give them a couple weeks and hopefully you’ll see someone dig in and realize their own weaknesses.
People like transparency. They want to understand why decisions are made, how an organization runs, and they want ownership. They want to feel like they’re making an impact.
Today we’re hiring more people who are willing to take cuts in salary in favor of larger variable pay and more stock because they want to feel that their day-to-day job is impactful and they have real ownership in what they’re doing. I think the secret is just being very upfront, very clear, and very transparent on goals and on the path to reaching a goal so people can be confident that they’re doing the right things to get to where they’re expected to go. The last part is accountability. We do stand ups and people put their metrics on the board. They’re accountable to me and to the gamification tools that we use, but the ultimate thing is SDRs are paired one-to-one with AEs. Their AEs are relying on them to produce pipeline and, because of that one-to-one relationship, they get a lot of benefits. They get good mentorship. They get way deeper into sales cycles because they have one AE to work with and they have long one-on-ones where they talk about the state of business in that territory. They also have a responsibility to produce that’s stronger than a lot of other teams. That helps a lot, having different sources of accountability and strong accountability.
I just do it by observation and through one-on-ones and sitting in the middle of the team. That way I can see if someone is not at their desk for a long time and seeing a person who may not be as engaged or as positive about their job. So for me it’s really just observation and time doing one-on-ones. I haven’t instrumented anything. It’s just observation and checking in.
I’ve found that it’s best to be absolutely upfront and incredibly transparent and to tell the team why a setback occurred and what we’re going to do, or ask them what they would do to help create a solution and grow. There are all kinds of setbacks, but those are the times when organizations improve and become more innovative and figure out ways to evolve. We’ve had to evolve a ton of times this past year, but it’s added up to a lot of positive things, as well.
Wins are super important, especially customer wins. So I make sure to talk about them a lot, create a fun team activity around them, and announce them at our all hands meetings. With a product- and engineering-centric company, there’s nothing better for engineers than to tie sales wins back to their work. There’s a big separation from what they do and what sales produces, so it’s good for our team and for the whole organization.
We talk about it publicly at team meetings and at our all hands meetings if it’s really big, like a customer win. I like to award people, whether it’s monetarily or with something that’s going to help them grow. It shows that we value them. Especially in a smaller organization, good visibility and good optics can mean a ton to people because it means that you’re singled out for the next big promotion. The smaller and flatter the organization is, a promotion can be a pretty big deal. For individuals, it’s giving them recognition and also showing that we really value them.
The word setback is big. For an individual setback, maybe there was a deal that was about to cross the line and didn’t go through. Individual setbacks are times where people can evolve and learn, and sometimes it’s the best opportunity to learn. When I got to MemSQL, I thought we should create more visibility into losses. If you’re going to be closing an opportunity, you should be forced to detail what happened if it didn’t close — not because we want to place blame, but because we want to learn. There have been times where we documented losses and learned, we shouldn’t be getting into deals where certain kinds of details are in place. For an individual setback, it’s a good time for an individual to learn to understand and embrace the loss and know what to avoid that in the future or take some sort of lesson from it.
Luckily I haven’t really had to discipline anybody. No one’s done anything actively destructive, but if it happened, you really just can’t hesitate. You need to jump on it very, very quickly because not only do you need to send a message to that individual that what they did was not appropriate and cannot be treated lightly, but it’s a lesson for the wider team and it’s a lesson for the organization. Tackling it as fast as humanly possible and making it very clear to the rest of the team what that form of discipline is so it’s not repeated. You can’t be afraid to take action. It sounds really obvious, but there definitely have been moments where I have seen situations where people just let things slide. That is silly I think because you miss a big opportunity and you could be creating a very negative effect by not putting it out in the open what needs to happen and what the consequences are for doing something destructive.
It’s a practice of empathy. I try to talk to each individual team member and ask a lot of questions to understand what about the other person’s actions was a problem. I ask what the other person did was a challenge, and then role play to step into the other person’s shoes and try to see if they can adopt the other person’s point of view. Finally I ask if it was them, how they would resolve this conflict? The end point is to help each party to force themselves to understand the other person’s point of view and then come up with their own plan. I’m rarely the kind of person who would invite all parties into a room and try to mediate it, butI would enable them to approach each other and resolve those conflicts themselves. I think it’s a good human skill to be able to handle conflict and I think the best way to do that is by forcing yourself to be empathetic. I want people on my team to be able to solve their person-to-person conflicts on their own.
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