A 2020 Crash Course: Three methods for Leading with empathy as a (new) SDR during a global pandemic

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Anyone that has ever been in a sales development role or sales dev rep (SDR) knows one thing for sure — it’s an unforgiving job. Day in and day out, you’re searching for potential customers that would benefit from your companies’ product(s) while trying to connect with them at a time when they can enter a sales cycle. This requires walking a fine line between being persistent enough to generate interest in what your company offers, without becoming a burden on someone’s inbox or voicemail (and getting a lot of nos in return). 

In my first year in the role this past year as an SDR, I’ve learned a lot about real-world persistence. How do you determine who would be a fit for the product? When is the best time to reach out to each industry? What is the best way to craft a compelling and relevant message? Through many experiments and a lot of coaching, I felt that I was finally learning how to find the right contacts, understand their business challenges, and offer them a compelling solution. 

And then cue 2020 and COVID-19… like everyone else, I had never felt more unprepared. Even just thinking about trying to promote a product throughout a global pandemic felt overwhelming. Most of those in the SDR role are new to the B2B technology sales world. I certainly kind of still am. We’re just learning how to handle rejection while remaining positive and trying to continue to add value in every interaction we have with customers. 

Adding the complexities and stresses of a global pandemic significantly complicates this learning. How can you continue to promote solutions, with prospects facing conflicting and constantly evolving priorities? With many businesses closing down, how do you justify an external investment? What kind of objections are you even going to have to work through? The uncertainty became almost stifling, especially for someone early in their career and new to a profession that requires years to master (if ever). 

However, with time and some patience, it feels as though I’ve received a crash course in resiliency, grit, and understanding that will change how I view sales for the long-term. I preface these learnings with the sentiment that there is no one size fits all or silver bullet approach in sales (as I’m sure you’ve heard before). 

I’ve found that leading with empathy during the last few months has allowed me to enable my company to continue to grow while ensuring prospects are feeling they receive value and are heard in every conversation. Below I break it that down to three methods. 


Pause and think about what is most important to companies right now. 

Be intentional about what you are sharing with prospects – whether it be content or your messaging. Now more than ever, everything you send needs to be hyper-relevant to your prospects while understanding the situation and the constraints they are currently facing. 

For my team, we thought it was best to completely re-write all of the messaging that we send to prospects. We took a week to pause and think about the pains our potential customers would be feeling, and how their goals would have shifted in reaction to the pandemic. With so many new and evolving priorities, the message needs to be extremely targeted to whoever you are trying to reach. Ultimately, you need to ensure that everything you share is worth investing their time into reading or learning more about. While this has always been true, it is clear that bandwidth is even further reduced during this pandemic, and any type of generic outreach will be ignored or, worse, received poorly. 

A big part of this will be doing your research; you can’t make assumptions. During every phone call or email reply, you learn more about how your prospects are feeling and what they’re thinking about. Another valuable method is hosting industry town halls or virtual meet-ups and applying those learnings to your outreach. You always want to appear as an industry expert, and speaking directly with those in the market will be the fastest and most accurate way to do so.

Keep in mind that sentiments will often change throughout the pandemic. The shift to a remote work environment will take time to fully develop and become efficient; however, talking about your new home office six months into the situation could come off as stale. Initially, I focused on just wishing prospects well as they went through the transition and offered myself as a resource until they were ready to look at tools to help them. This could take the form of helpful blogs or videos, as well as sharing any learnings from other industry professionals during the town halls. I’ve now started to focus on how their day-to-day routines and workflows have changed, and to help them understand where there are bottlenecks that could be improved. 


Share impactful resources that aren’t just about your product. 

Now is the time to share content that can help your prospects – even if they aren’t quite ready to buy your product. Position yourself and your company as thought leaders in the space by sharing resources you’ve made or helpful ones you’ve found from other industry experts. By acting as a resource and offering value before you ask for their time, it leads to a warmer first conversation. 

Especially now (or really ever), you should not be just “circling back” to “check-in” and see how your prospect is doing. We are all trying our best to manage chaos right now, so every touchpoint should be relevant while also insightful. This might result in a shorter outreach sequence or more spaced-out touchpoints, but you will gain more respect from your prospects. Continually pinging someone without providing anything will likely result in more than one angry reply in your inbox and leave a lasting poor impression. 

By leading with educational and resourceful content, you are setting yourself up for a much more strategic conversation, whether it be now or in the future. These resources can set the base for your conversation and allow you to dig deeper with your prospects as you have a neutral starting point for the discussion. 


Make it human. 

I cannot stress this enough – there is always a person on the other end of your outreach. Being in a role that is so heavily measured by activity and output, it can be easy to feel like throwing out an extra couple of mediocre emails won’t have an impact. Sometimes it even feels like you’re just sending messages into the abyss. However, at the receiving end is a person that will work at multiple companies and likely across industries throughout their career. The impression you make of both yourself and the company you represent will be taken with that person and could lead to either positive or negative interactions now and in the future. 

Considering the challenges that everyone is facing right now, and the resultant set of stresses and priorities, people just want to buy from and work with people they can trust. That starts from the very first email and call and will build throughout the sales cycle. By making sure your messaging is relevant yet ever-evolving and sharing impactful content, you set a strong foundation. However, what I have found most powerful throughout the last few months has been showing my personality. 

We’ve all fought over a kitchen table seat or the most comfortable part of the couch, and who hasn’t had a fire alarm interrupt a Zoom meeting (or several). Sharing experiences and light-hearted jokes around matters like these show your prospects that not only are you human and share the same challenges but that you’re not just pushing one agenda of a quick sale. You’re setting yourself up as someone they can trust and enjoy a conversation with, instead of feeling that they will be forced into a sales cycle when they aren’t ready to evaluate. 

When the only interactions everyone is having is through screens, it can really change the tone of a conversation to add in a small joke or a gimmick to help diffuse the stress most prospects feel when they get the dreaded cold sales email. When you combine this light-hearted tone with a researched and relevant message, you’re going to start off the relationship with more trust and openness to learning. 

 From there, go at the pace of the prospect. While it is always important to foster transparency and honesty about intentions and timelines, now is not the time to aggressively push potential customers. Sometimes people are afraid to say no and will give you an excuse, but during such a challenging and uncertain time, I have found it impactful to take specific objections at face value. Budgets have been cut for the remainder of the year (if not longer), there are concerns about maintaining your team or still growing into a new market. Sometimes the timing just isn’t right for new investment, and being respectful of that will help you further build your relationship with a prospect. Opening up an opportunity to reconnect in 6 months is better than burning a bridge forever.


At the End of the Day…

Companies will always find ways to adapt and evolve, no matter the challenges they may face. However, behind those decisions are people that are just trying their best. While it may seem simple, keeping this in mind while you are trying to continue to do your job to generate interest in one of the thousands of products (in the middle of a global pandemic no less) will get you much farther than you think. By being relevant, impactful, and not being afraid to see your personality, you’ll be able to show each prospect that you really do care about helping them solve their most pressing business challenges. 

This new reality presents an opportunity for SDRs to position themselves as partners to business leaders across the globe. No longer do we need to be stereotyped as aggressive or an annoyance, but as a thought leader and resource that can add value from the first interaction.  

Nicole is a 2019 RBC Honorary Fellow recipient, and a 2019 VFC Fellow. Nicole is an outbound sales development representative at Loopio. She studied business at Western University. She is interested in writing about SDR best practices, sales enablement, and social entrepreneurship.

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Nicole Plant is a 2019 RBC Honorary Fellow recipient, and a 2019 VFC Fellow. Nicole is an outbound...