9 Lessons I Learned the Hard Way: What to Avoid to Become A Better SDR

Jamie Shanks
Jamie Shanks

9 sales reach out mistakes

Like many B2B SaaS sales reps, I became a Sales Development Rep (SDR) fresh out of school. I always wanted to be in a role where I controlled my own destiny and my success was a result of how hard (and smart) I worked. Looking back on my first 6-7 months in the role, I’ve been fairly successful, but when it came to my work ethic starting out the “hard” sometimes outweighed the “smart”.

We all like to think we’re perfect, yet no matter how hard you try, there will be some facepalm moments when you’re trying to reach out to really smart people at scale.

I got fantastic training and onboarding at Uberflip and had a ton of support from the team during my ramp up period. But no matter how much training you do, you sometimes have to take your lumps to get better in sales. For all you future SDRs, here are some of the most egregious mistakes I have made. I wanted to share them in hopes of saving some of you the embarrassment.

Disclaimer: While this is meant to educate brand new SDRs, it’s also an apology to marketers. I know I’ve probably made it into a few “halls of shame” for some of these missteps!

1. Sales Automation Fail

If I’m going to expose some of my early career mistakes, I may as well jump in with the most cringe-worthy of cringe-worthy offenses: Sales Automation Laziness.

Sales automation is super helpful. It allows SDRs to put prospects through a cadence of touches where engagement is tracked and workflows are pre-determined. It’s amazingly helpful for managing your lead pipeline and making sure you are following up with everyone.

As the SDR, it’s my job to create the value and earn the right to a conversation. In this case, I threw the prospect into an automated task without checking that all of the data pulled through or proofreading. I clearly didn’t take the time to add value or attempt to educate either.

bad automated sales email

Yikes. Can you guess what the response was? Perhaps the fastest (and most warranted) “take a hike” email I’ll ever get!

This is a mistake I only had to make once. You can send out a million generic emails and get nowhere – more often than not it will bring negative reactions towards yourself, as well as your company. When we as SDRs bring value with every touch, whether it be email, social, or phone call, we build a case that earns us the right to have a conversation. With sales automation, err on the side of personalization.

If you want personalization at scale, I suggest the 10/80/10 rule where the very start and end of the email are personalized to your specific prospect, while the meat of the email contains messaging  that will largely resonate with an entire buyer persona or role you are targeting.

Read up on how you can reach out to leads without pissing them off.

2. Social selling doesn’t mean moving your pitch over to LinkedIn

Every SDR has heard statistics like “78% of salespeople leverage social media to outperform their peers” – but what does that really mean? How are all of these reps crushing their quotas using social?

My immediate reaction was to hop on social and make some pitches on those channels to mix things up a bit (I’m sorry, I swear). When you’re a brand new rep, it can be hard to think about the long-term – you have to hit quota and succeed now. But social selling isn’t some quick fix to hitting quota.

It is a goldmine of information and a place to share helpful content with your network. Treating it as the place to pitch when your email doesn’t get a response and your phone call doesn’t get answered is bad news. Here is me at the start of my sales career, (aka a marketer’s worst nightmare):

LinkedIn social selling email

This is lesson 101 in How NOT Sell to Marketers. Selling has always been social, and always will be. Leveraging social media is about using those platforms to deliver value and be helpful, just like all other selling activity.

Now I use social to listen to my prospects. I can identify the people within an organization that I should be talking to and it helps to learn more about them before we actually meet. When there is an opportunity to help, I can deliver information in a relevant and personal way.

Follow these 3 steps for knocking your social selling out of the park.

3. Fish where the fish are

I imagine the Ideal Customer Profile (ICP) is something ingrained into the mind of every SDR out there – and with good reason. Your ICP makes it easy to understand the qualities of the organizations that will find the most value in your product, and will bring the most value to your company. In other words, as SDRs, we need to be living and breathing the goals and challenges of these organizations.

The only problem in B2B SaaS sales is that your ICP prospect is the ICP prospect of 100 other vendors – I guarantee it.

When your dream prospect is seemingly impossible to reach it can be easy to fall into the trap of chasing and demoing people who will never be able to buy your product. Rejection sucks, but when someone is happy to talk it feels good! However, if you’re going to be trying to fit a square peg in a round hole it’s not an efficient use of your time.

You may have a bunch of positive conversations, but when it results in zero opportunity for the account executives you can find yourself in a desperate situation at the end of the month (which makes way for a bunch of other hard lessons that we will get into shortly).

Are your prospects avid blog readers? Try getting in the habit of blogging more.

4. Personalize your messaging

When I walked into Uberflip I thought I was going to be crushing quota from day 1 – “I know our product so well it helps marketers do A, B, and C – how hard could it be to have some conversations?”.

The fact of the matter is your best prospects will be the best prospects for dozens of other SaaS sales reps, and they are busy without even factoring in all of the sales outreach! It has been reported that business folk receive and send on average 130 emails per day. Gulp.

To break through the noise you MUST make your message resonate. This goes beyond product features and benefits. How do you make a specific prospect feel something or laugh? I’ve found humor to work incredibly well in my sales outreach. What I personally like to do is give a quick scan of their social profile to get a nugget from their personality that I can relate to or make a quick metaphor about.

personalized sales email

Bonus lesson I learned the hard way: going too deep into social profiles can backfire in two ways:

  1. Time consuming

  2. Gets you pegged as creepy

Chrome Extensions like Rapportive and Crystal help to personalize messaging and nail the tone of your emails without having to go all over the place to find the information. Thoughtfulness has always resulted in better outcomes even if it doesn’t result in a sales opportunity. I’ve developed some great relationships that started with a quirky email!

Check out some other Chrome Extensions that can help you create more engaging sales emails.

5. “Just following up/checking in/touching base”

I made this post because I’ve had my fair share of facepalm moments to start my sales development career (and I’m not alone). I’ve had incredible training and onboarding support here at Uberflip, but sometimes you just have to make some mistakes to learn. For this reason, I don’t want to get preachy with this post – but one of my early mistakes is now my pet peeve as a sales rep.

Stop “just following up”.

Add “just touching base” and “just checking in” to “phrases we should abolish from our vocabulary”. These are annoying ways to prod people until they respond to your outreach. It essentially tells the prospect they haven’t fulfilled your preferred response or timeline.

So what can you do to stay top of mind without being irritating? For one, sharing content can be a great conversation starter. Whether it be over email or social, sharing content that helps with a prospects challenges shows you’re paying attention and are equipped to help. In order to make it more engaging and give my contacts a preview of the content I’m sending them – I use our Chrome Extension, Shout.

share relevant marketing content

Again, if you don’t have a reason for contacting someone aside from “following up” then you shouldn’t send that email or pick up the phone. Anytime I’m about to call a prospect I make sure I can finish the sentence “I’m reaching out to you today because _____”. This forces me to step back and make sure I’m trying to bring value to the table, and not poke someone until they answer.

Make your follow up count with 7 ways to reach out to cold leads.

6. Respect timelines

In his book, Fanatical Prospecting, Jeb Blount speaks about The Universal Law of Need and how it governs desperation in salespeople. The more you truly need something, the less likely you are to get it. When all of your hope rests on a few accounts you get desperate and your risk of failure increases exponentially.

When you’re a brand new SDR, you have very few leads and little experience. It makes sense that you will have a tiny pipeline of engaged prospects. Everything that happens with those prospects can feel like life or death, but trust me it’s not. There were a few instances where someone wanted me to get back in a few months and it was crushing – how would I meet my quota this month?! So I tried to condense that timeline (respectfully of course) and pushed that person away as a result.

If I had just respected the timeline I was given back then, I’d be in a much better position now! No one cared – or will ever care – about my quota. If you keep your activity high and trust your sales process the results will come. In my experience, nothing deflects results like desperation.

7. “Send me more information”

In B2B SaaS sales this is an extremely common objection. At first, this sounded like a small win to me; however, any experienced SDR knows exactly how this went…

  • “Thank you for the opportunity – I’ll get a bunch of resources together and send them your way ASAP”

  • Spend 15 minutes drafting the “black and blue email” where I would take content from all over the place and send an email with 7 different hyperlinks.

  • Crickets…

Many people find this route easier than saying no to the sales rep. Oftentimes saying no will either result in conflict or a response as to why the prospect should take a meeting anyways.

Uberflip is a platform for marketers to create and optimize incredible content experiences, so we have a lot of content ourselves. It’s great that I have lots to draw on, but what do I actually send to the prospect? I like the what/when/why approach when dealing with this objection to understand if it’s even worth sending information in the first place!

  • What information would you like to see?

  • When would you like to see it by?

  • Why would you like to see it?

These questions don’t have to be asked in this exact manner, but they are easy questions to answer for someone who has any interest in what you are planning on sending over.

In the instances where I can send helpful information to someone, I use Target Streams to do so. Instead of sending a prospect to every corner of the internet to find the content I send, I can create a contextual content experience just for them and send it over under one link.

Uberflip Target Stream

Learn how content can become your best friend when closing a deal.

8. 3×3 research is meant to be quick

Despite all of the mistakes I’ve been exposing here, I really was a careful SDR! Too careful sometimes. Steve Richard of summed it up perfectly with the contrast of two SDR personas: The Cowboy and the Librarian

Cowboys shoot from the hip. They make tons of calls and their pitch is largely the same to everyone. They sacrifice some research and personalization but make up for it in pure volume.

Librarians spend all day doing research on two accounts and make exactly two phone calls. When I came into my new role I was very fearful of what could happen. What will they say? How will I respond if they say X?

So I would scour their social accounts and past blog posts looking for every single piece of information on the prospect on the off chance it came up. The problem with this is that the majority of calls you make result in a voicemail.  At the end of the day I’d feel like I did a ton, until I looked at my call log and realized my day was wasted researching for voicemails.

What we tell new SDRs at Uberflip is that you don’t need to know the prospect’s blood type to have a productive conversation.

3×3 research means find 3 points in 3 minutes about your prospect. Points that will make your outreach relevant – without spending all day researching. The perfect balance between efficiency and effectiveness.

For my 3×3, I like to start with one thing about the prospects company, one thing about their role, and one thing about them personally that can make my message resonate.

9. Remain positive – everyone messes up!

Well SDRs, there you have it. My list of biggest and most embarrassing mistakes. Those of you who made it this far down are probably thinking, “There is NO way I would make some of those mistakes” – and I hope you’re right!

However, when pressure kicks in and things get hectic, you may very well make some of these mistakes yourself. The key is to remain positive.

Being an SDR is rejection-heavy, difficult work. But it’s also the most enjoyable and rewarding work I’ve ever done. If you love your product and your team, you get to go to work every day and share that with as many people as possible.

So when you inevitably slip up here and there just pick yourself up and learn from it!

Get your content in on the deal. Read our eBook to learn how content is for closers.

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