SDR Leadership Lessons from the All-Star Sales Experts

Being a Sales or SDR Leader is not just a privilege, it’s also hard work and a huge responsibility. It takes some grit to become one, but it definitely requires more than that to succeed as a leader and bring your team to success as well.

For some it might take years to figure out how to do that. Others learn their lessons fast enough.

Whether you’re only planning to take on the role of an SDR Leader or have been in that position for some time, it’s always a good idea to listen to your peers and learn about their struggles and insights.

So we asked 10 top experts to share some of the leadership lessons they learned the hard way to give you a head start in your career and help you avoid some of the SDR management pitfalls too.

Let’s see what they have to say.

What are some of the most valuable lessons you’ve learned as an SDR Leader?

 

Morgan J. Ingram

Morgan is the VP, GTM Talent and Development at Sales Impact Academy. He has been named one of the Top 50 Sales Leaders to follow by LinkedIn, a Top 25 Sales Development Thought Leader by Inside Sales, and LinkedIn’s Top Sales Voices of 2018, 2019 and 2020. 

LinkedIn

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The most important lesson for an SDR leader is that you work for your people. They don’t work for you. Be proactive in giving your feedback, talk to your team daily, and get in the trenches with them. When you show you can do the work, your entire team will love you for it and will follow you through the hard times.

 

Joey Williams

Joey Williams is the Senior SDR Manager at Chili Piper. In this role, he handles processes, strategy, and coaching.

LinkedIn

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One theme that has occurred in my time as an SDR leader is the importance of vulnerability – both from reps and from leaders. SDRs have an inherently vulnerable job – they’re putting themselves out there all day every day and facing rejection. Oftentimes, that rejection feels personal and some prospects will make it very clear that, for them, it is personal. Because of that, we’ve always known that the role itself requires vulnerability.

What has become clearer over time as we’ve evaluated our onboarding and coaching processes internally is that two-way vulnerability between reps and their managers is essential for a healthy environment of growth.

On the reps’ side, we often take for granted how much it takes for a rep to want to share their mistakes. Especially when they’re struggling, honest discussions with their manager about what is going wrong is sometimes the last thing they want. 

In some cases (such as a cold call gone wrong), they’ve already put themselves out there for the prospect – and gotten rejected. Now we’re expecting them to share the call with their manager and look like they don’t know how to do their job? 

Reps on your team need to know that failing is inevitable, mistakes are inevitable, and the best way to move forward is to own the mistake and learn from it. Creating an environment where reps aren’t afraid to fail in front of their managers is a great way for this growth to happen. When reps struggle, this trust will be key to improvement.

As for building trust… That brings us to vulnerability from managers. How many people have been asked to be vulnerable with their managers but not gotten it in return? It’s difficult to have a true environment of vulnerability without the manager embodying the same actions they’re expecting from reps. 

When coaching reps, managers will often want to have all the answers immediately. Fight. This. Urge. When your rep needs coaching, be curious with your reps the same way you expect your reps to be curious with prospects. This includes admitting when you don’t know the answer instantly. When you are open about trying to solve a problem WITH your reps, instead of FOR your reps, you’ll find creative solutions you didn’t know existed. 

Just like you can’t copy-paste your way to being a successful SDR, you can’t copy-paste your way to being a successful manager. Let go of having all the answers and work WITH your reps to find the best path forward.

 

Gabrielle Blackwell

Gabrielle “GB” Blackwell leads outbound sales development representatives at Airtable for their Strategic Accounts segment. She’s been named a Salesforce Top Sales Influencer, a LinkedIn Top Sales Voice, and a LinkedIn Sales [In]sider for the content she shares about sales, sales development, and leadership.

LinkedIn

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The most valuable lesson I’ve learned as an SDR leader is the importance of well-delivered and timely feedback. Well-delivered feedback is specific, it’s actionable, and it’s pointed at the problem not the person. Timely feedback means that it’s given at a time when someone is able to receive that feedback and apply it in a meaningful and impactful way. Taking the time to develop the skill of providing feedback is key!

Maurizio Cappitta

Maurizio is the Head of Sales Development at Workpath. Born and raised in Malta, he moved to the UK in 2008 and soon found his first ever role as an SDR. Today he is based in Germany, where he leads the global SDR team at Workpath. Having amassed 14 years’ worth of what he calls “mistakes and embarrassments,” he offers his support and mentorship free of charge to SDRs and SDR Leaders who are willing to “avoid doing the same mistakes he has done in the past.” 

LinkedIn

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With the exception of simple, transactional sales environments, SDRs are most effective when they understand what they are doing. Role plays, call shadowing, and handholding go much further than call scripts, checklists, or managing by volume (tracking calls or emails).

Let’s briefly explore some of these points.

–  Call Scripts: Calls don’t always go according to plan, of course. So when we give our SDRs an easy-to-follow script, and a call derails from the script, we’ve got to ask ourselves “how did I set up this SDR to be successful?”

What we need, instead, is to equip our SDRs with the relevant (i) knowledge and (ii) training experience to navigate the unexpected, to maintain call control, and to bring it back to the desired point. We’ll revisit knowledge later, but for the time being let’s explore that second point – training experience.

–  Training experience: Has anyone on your team(s) been through a scenario such as the following? They have completed the onboarding process, they go live, they have a script and the “SQL Criteria” but they suddenly freeze. They feel as though they don’t know where to start, what to do, or how to talk to a customer.

That’s because SDRs don’t want to trip up with a live prospect. They don’t want to seem incompetent, nor to make the company look bad. So they stall, and anxiety engulfs them. Sure, they have listened to several calls with their peers and/or their buddy, but is that enough?

This is all a little like learning a language. We may have heard it being spoken several times. We might even have a dictionary, and a list of phrases we will most likely need to use during a holiday. Does that mean that we’re ready to engage with the locals, even if to ask simple questions such as asking for directions or to ask for the bill at a café.

What works instead is role-playing. I’ll be the first to hold my hand up and say that they’re enormously time intensive, but I’ll let you in on a secret: Three to four hours or role-plays this week will have a multiplier effect in the future – both with regards to time saved in coaching, and consequently in quicker ramping.

So in summary, what SDRs really need to be successful is a great onboarding process. Watching videos and reading material are important, but they can only go so far. Human intervention (i.e., us working with them, handholding them, and investing the right amount of time ensuring they understand what they need to do) goes a long way to ensure they feel confident and ramp at the desired rate.

Failing to do this upfront means we’ll have to spend that amount of time (and maybe more) down the line: coaching, correcting bad behavior, engaging in performance management processes. Invest your time today for an easier tomorrow.

 

Ben Pearson

Ben Pearson is currently the Head of Sales at Navattic. He formerly sold at companies like Square and Front.

LinkedIn 

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I think the best way to promote strong SDR performance is give them guided freedom. Being an SDR is a grind. The best SDRs I’ve worked with and coached are those that find a strategy/vertical/cadence that they’ve created and have success with. And I let them run with it. I think it can be easy to want to control every move of someone who is somewhat new to Sales. But empowering your SDRs to try new ideas and encourage them to find success in their own ways resonates the strongest.

 

Witold Solski

Witold Solski is the SDR Manager at CloudTalk. He is an experienced leader working in many diverse industries from O&G through heavy industry all the way to SaaS. Witold has been working in Business Development for years and has successfully led diverse teams for many global brands such as Amadeus, Panasonic, IATA, KPN.

LinkedIn

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During my work as an SDR Manager, I’ve learned that there are three key elements that you need to master if you want your team to be successful:

1. Always spend time with newcomers.

Spending an adequate amount of time with new team members during the onboarding phase is crucial to ensuring their long-term success at your company. It’s an investment that really pays off. 

Onboarding is the time for creating good habits for your new team members and making sure that they have a good foundation on which to grow. It’s also when you establish mutual respect and trust among the members of your team.

2. Don’t just manage — lead. 

This is a more demanding path, but again, it is an investment. Coach your people, lead them by example and support them.

Very often we get swamped with the amount of reporting, planning, and everything else that being a manager demands of you. Make sure this doesn’t dominate your relationship with your team. Your SDR management priority needs to be your team’s development over time.

3. Be decisive.

Business Development is a very demanding and fast-paced environment. Make sure to always give clear instructions to your team. They need to know that you are confident in your decisions and the reasoning behind them. If your team understands why you’ve decided to focus on a certain strategy, they will no doubt achieve better results.  

 

Dipak Vadera

Dipak kick-started his sales career at Uber and Hootsuite witnessing growth that would influence his future strategy. Currently, he’s leading the EMEA Sales Team at Leadfeeder and is on a mission to help B2B companies nail their prospecting efforts. He’s a self-proclaimed “Fulltime Backpacker” and a strong advocate for remote work. Dipak balances work and travel by staying no longer than 3 weeks in one place.

Website  | LinkedIn

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One of the most important lessons I’ve learned as an SDR leader is setting realistic and data-driven goals for my team. It’s even more important in a remote sales environment.

Secondly, give your team the tools they need to be successful. It’s almost as important as hiring the right people.

Last but not least, don’t get hung up on activity metrics; it’s not all about quantity. This hinders and limits creativity. Don’t just count your teams’ conversations – help make their conversations count.

Zakk Williams

Zakk Williams is Head of Partnerships at Better Proposals, an online platform that allows customers to easily build, send, and track beautiful web-based sales documents. He is an award-winning graphic designer, a guest speaker in digital marketing and sales strategy, and has over 15 years’ experience working in digital media and brand development.

LinkedIn

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Being a leader is not just a title. It’s a responsibility.

A great salesperson is like a Swiss Army Knife. They need an array of tools (confidence, persistence, empathy, and the ability to listen and problem solve) but they only function effectively when those “tools” are well maintained. 

A leader provides. A leader sets goals. They hold themselves accountable and encourage their team to do the same. And in doing so, they build a positive and motivating work environment and a culture of collaboration, innovation, and support.

When it comes to building a superstar SDR Team, 4 of my most valuable lessons are:

1. Good training creates repeatable results

Many will be familiar with the quote, “The definition of insanity is doing the same thing over and over again and expecting different results.” But in my experience, systematic training and repetition creates repeatable success, which is our goal.

Ensure your training program is consistent and includes product knowledge, buyer personas, outreach and follow-up processes, prospecting and a consistent approach to tracking, and your SDRs will feel competent to deal with most situations and deliver results.

2. Within that training, encourage listening, not selling

Studies have long shown that allowing someone to talk about themselves stimulates the brain’s pleasure response, building trust and improving the perception of the listener.

Train your team to let your client talk.

Open-ended questions will reveal a client’s situation, problems, implications, and needs (SPIN) and allow your SDR to quickly qualify their suitability and empathetically position your business as the self-defined solution.

3. Check in, don’t check up

Most SDR situations necessitate monthly sales quotas, but this can often be overwhelming for sales reps and few people enjoy micromanagement.

Be a true mentor to your SDRs. Let them learn and grow from your experience, give constructive feedback, reward all wins (big and small), and illustrate the trajectory of success. Many sales professionals are just as motivated by status as they are financial compensation. And if you’ve done your job as a leader well, they won’t be an SDR for long.

4. Encourage healthy competition 

SDRs, like any sales professionals, tend to be driven by ego, and are competitive by nature. 

With the benefits of gamification being well-documented, creating light-hearted competition that aligns with performance goals (whether it’s for one day or a whole month) can often break the monotony of endless emails and calls and keep SDR’s driving towards success.

 

Meg Bounds

Meg is the Head of Sales Development at Ebsta. She works alongside leadership to strategize and formalize sales development processes across EMEA and the US. Her SDR team is responsible for sourcing 2/3 of AE pipeline.

LinkedIn

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The most important lesson I’ve learned is that no one cares what you do. Prospects only care about what you will cause their company to do when partnered together.

For example, there’s no point starting a cold call with “I work in the predictable revenue industry” – that’s all about me. 

But to start with “I help you close deals faster by taking the guesswork out of sales”… Well suddenly it’s a more interesting conversation!

And what is repeated back to you by your prospect is your email subject lines, your meeting titles, your follow-up calls only works to reinforce what you can do for them each time you speak!

 

Alex Dzhurasenko

Alex is an Account Executive at Reply. She acts as a sales engagement advisor for the EMEA region. She is currently building her own team of AEs and handling most aspects of the sales process — from discovery and product demos to closing.

LinkedIn

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First, I have to say that I’m a newbie Sales Leader, only transitioning to the role. And the fact that we’re working remotely definitely makes my experience less ordinary. Yet, studying psychology definitely helped a lot!

That said, I believe that my first priority as a leader is to create a friendly atmosphere within the team to give its members a sense of belonging and support. That is why we have regular team calls and dedicate some time to discussing personal issues.

The same goes for coaching and onboarding, which is impossible to do in person when working remotely. To address this challenge, we’ve created an extensive library of educational materials to provide the required resources on-demand whenever the SDRs need them to address current challenges or for self-development.

Speaking of personal development, we do pay attention to it regularly. For example, we hold one-on-one calls every week where we analyze the performance of the rep during the week as well as set new goals and work out a strategy to achieve these goals. We make these goals attainable and come up with practical skills or actions that can be taken to achieve them. 

Accountability is also crucial for SDR management in a remote team. It’s me who’s accountable for my team’s performance first of all, and that’s the only way I can demand accountability from the team. However, we do have a pretty flexible workflow. As a team, we develop a workflow or template, put it to work, and check a week later to analyze its performance. Then we decide how/whether to move forward with it, and adjust it if needed.

The war in Ukraine, where most of my teammates are located, necessitates its own adjustments. Just a few days ago, during a major missile attack on multiple cities, we had to reschedule our regular call because some of us had no electricity while others were taking shelter away from their homes. This is where that flexibility and empathy a leader should possess comes in really handy.

Key takeaways

So the experts have spoken. As you can see, there are some common challenges that they face as well as specific takeaways that you might want to consider as you move up the career ladder as a sales professional.

To wrap up, here are some of the fundamentals that could make you a successful SDR leader:

• Empathy. Sales development can be stressful enough so don’t give your team more reasons to quit. Rather than being afraid to fail in front of you, your team members should feel comfortable about discussing their struggles and solving them together.

• Accountability and trust. Don’t just keep your team accountable — acknowledge your accountability too. And make sure to give your team some freedom to make their own decisions.

• Feedback. Having open communication with the team lays the foundation for fruitful cooperation and creates a friendly and nurturing atmosphere.

• Coaching. The best investment you can make as a leader is the proper SDR onboarding and training. Giving knowledge and tools to your team will soon pay off – both in terms of performance and tenure.

• Purpose. The sales objectives that you set for your team should be clear and attainable. Don’t try to shoot for the moon, better lay out a plan to achieve what really matters. Knowing what to do is just as important as knowing why you should do it.

And most importantly, remember that your team doesn’t work FOR you. In most cases it’s you who should be working for your team’s success. 

As they say, don’t manage – lead, and success will be yours.