As a Sales Development Representative (SDR), chances are you’ve heard some version of the following story.
Two shoe salesmen go to a remote island to break into new markets. After a few days, one salesperson calls the office and says, ‘I’m on the next flight. Can’t sell shoes here. Everyone goes barefoot.’ The other salesperson sends an email to the boss minutes later: ‘Get ready! The prospects are unlimited. Nobody wears shoes here!’
Why is this story important?
Because it illustrates the greatest hack for growing as an SDR: attitude.
According to Lori Richardson, a thought leader on B2B front-line sales growth, attitude is one of the few things one can control, 100%, in a selling or SDR/BDR role.
“I can stop making excuses for Q2, or the first half of this month, or for my lack of interest in this role. I can be the CEO of my role.”
While attitude is important, it certainly is not the miracle drug to level up your career as an SDR.
We bring to you 11 unconventional pieces of wisdom from veteran sales leaders that will enable you to stand out from the competition and accelerate your ascent to the top.
Let’s get started!
1. Be fearless: Jon Dion, VP Sales at Auditboard
As the VP of Sales at Auditboard, one of the most frequently asked questions Jon encounters is about the qualities of top Account Executives or future sales leaders.
While he has a ton of advice collected from sales experience that spans close to a decade, some of his top recommendations include focusing on revenue-generating activities, cultivating the ability to inspire trust in people, and being fearless.
“There's a difference between trying to win the game, and not trying to lose.
Reps not trying to lose focus on things like what their Business Development Representative (BDR) is doing, what other reps are doing, what their Chief Revenue Officer (CRO) is doing with territory changes, and not making mistakes. They're playing defense. Reps focused on winning know a TON of customer stories, know the product better than their peers, have a POV to present the customer, like making friends at the C-level, and so on. They're playing offense.”
And he’s not the only one to feel this way.
A very popular quote by George Addair, founder of The Omega Vector, goes: “Everything you've ever wanted is sitting on the other side of fear.”
2. Authenticity trumps everything else: Michael A Rosenberg, VP of Sales at RocketReach.co
When we reached out to Sales expert, Michael A Rosenberg, to know the one hack that would enable any future sales leader to radically level up their career, he was brutally honest.
“There is no silver bullet for anything. Many people are looking for the "answer" to sell and there just isn't one for almost any situation.”
There is however one thing that worked for him throughout his long career in sales (over 14 years in impressive roles with companies such as Square, WorkWave, and now RocketReach, among others).
“I've always felt authenticity does it for me. When you have a conversation with a family member or friend, and convince them to do something (sell) you don’t speak in a higher pitched voice, you don't use jargon, you are yourself "
This is often the golden rule for reps to remember. Trying too hard can make you come across as too pushy or too sales-y.
Michael emphasizes that it’s essential for him as a salesperson to believe in the product and definitely need to know it will work for the prospect.
“It's why our discovery call is actually called a Fit Assessment, to ensure that we fit, that I solve an actual problem. Not all are like that, but I'm not the type of person who is going to be selling ice to an eskimo.”
3. Indulge in some self-deprecation: Charlie Locke, Head of Sales at Circle and Co-founder of SDR Nation
As Co-founder of SDR Nation, a membership community meant exclusively for SDRs, Charlie is passionate about helping SDRs nail their job and get promoted. So much so that this mission statement is also his LinkedIn headline.
In one of his letters to this community, Charlie shares a classic, timeless piece of advice for SDRs on how to build a rapport with their prospects.
“Everyone talks about the importance of rapport building, but they rarely talk about the how. It tends to simply be a throw away tactic, something you have to do before you segue over to business. And guess what, if you treat it as such, it comes across super inauthentic (and you would be better off simply not doing it at all).”
When I'm building rapport, I'm trying to humanize myself in a truly authentic way, by being relatable. I want them to know I'm a real person with flaws and all, not some perfectly polished sales bro.”
He adds:
“The art of self-deprecation (making fun of yourself) is the answer. Self-deprecation has been used by speakers, comics, and sales people for years as an icebreaker, because it's very easy to do…and is always authentic.”
He then gives an example of an unconventional cold call for SDRs to become more relatable:
Buyer: "Hello?"
Seller: "Hi Janielle, it's Charlie here from SDR Nation how are you?"
Buyer: "Um, I'm good. How are you?"
Seller: "I'm OK I guess, my 4 year old decided to wake up the entire family this morning at 5:30AM so I'm a bit tired to say the least! hehehe... The reason I'm calling is…"
This helps because it shows the buyer that you’re not perfect, nor trying to be. You’re human, just the way they are and you go through the same highs, lows, challenges, and struggles of everyday life. The self-deprecation makes you more relatable and more trustworthy.
4. Stop shooting over proposals: Nate Stoltenow, CRO & Founder of Humble Co.
From being an Account Executive at the Sundance Film Festival to climbing the corporate ladder right up to being the Vice president of Sales at Expert Voice, Nate has donned many hats in the sales profession.
He is currently also Sales Advisor to many B2B companies including Plena, Nivati, and OTW Safety, in addition to being Founder and CRO of Humble Co., a B2B Sales Agency.
His one piece of advice for SDRs, especially those selling complex services, products or SaaS is to be in the driver’s seat, always and leave money on the table, never.
For this, he suggests two things:
1. Stop ‘shooting’ over proposals
“Often I hear salespeople say this post demo: ‘I’ll shoot over a proposal for you this afternoon. When would be a good time to follow up?’
Next time, try this: ‘I can have a proposal together in the next two days. Does Tuesday at 2pm work to review it together? Pull up your calendar and let me know if that time works’.”
2. Schedule a ‘back stop meeting’
“At the end of your proposal review meeting – start implementing a ‘back stop meeting.’
Here’s what you can say: ‘Sounds like it’s going to take a few days to review this proposal. Let’s talk at the same time on Tuesday so we can cover any questions or concerns that might arise between now and then.’
A back stop meeting helps ensure you don’t chase.”
5. Be paranoid about your demos: Florin Tatulea, Head of Sales Development at Plato
As someone who successfully went on to become an AE and Sales Manager from a founding SDR at Loopio within a span of 6 years, Florin is well-positioned to dispense insider tips on sales career growth.
He believes that there are “a number of things top reps do well that are not always very evident or discussed in onboarding, sales training, or in your sales methodology.”
And one of them is being paranoid about their demos happening.
“They don't just assume that prospects are going to show up. They have a diligent process to engage with prospects between the time the demo is booked and it occurring.”
He advises SDRs to take care of these three touchpoints when the demo is one week out.
- Summary email of their initial discussion
- One email providing a piece of content that’s valuable with no ask
- Email intro to the Account Executive a day before the demo
6. Book your meetings for sooner: Tito Bohrt, BDR/SDR Advocate
A BDR/SDR advocate, Tito Bohrt is the CEO of AltiSales, a company that aims to offer world class training to SDRs and execute sales development for organizations.
After analyzing 6414 meetings, one of his top pieces of advice for SDRs is to book their meetings for sooner.
7. Invest in self-education: Richard Harris, 2021 & 2022 Salesforce Top Sales Influencer To Follow and Founder, The Harris Consulting Group
With over 25 years of sales’ experience under his belt, Richard Harris is one of the most reputed names in the industry.
He has been conferred with various tokens and awards over the course of his career including being crowned the Top Sales Leader five times by The American Association of Inside Sales Professionals and the Sales Leader to Follow, twice, by Salesforce.
He shares his biggest pointer for aspiring sales leaders: Invest in self-education.
Many organizations don’t possess the infrastructure to teach their SDRs everything they should know. Especially smaller teams find it hard to dedicate as many resources to sales development.
So it’s essential that the initiative comes from the reps themselves. It is on them to ask questions, seek information, explore educational resources, engage and interact in networks, and build their skills so that they can not just survive but also thrive and reach the next stage of their careers.
8. Have people in your corner: Sarah Brazier, Account Executive at Gong
Having transitioned from an SDR to a Mid-market Account Executive within a span of three years, Sarah shares how having people in her corner made all the difference for her.
In a LinkedIn post, she describes an incident that happened while she was running a Proof of Concept (POC) trial for Gong at a company. The company ended up making a leadership change right when her deal was all but done.
Sarah had been nurturing the account for a month, sharing how-to’s, tips, articles & best practices for her target audience, and building their trust.
She had involved everyone on the trial, single-threading power-users and customizing their instances to know the impact of having/not-having Gong for them.
Unluckily, the new leadership knew nothing about this project.
“Overnight, my deal that was a sure-thing became a best case at best.”
So, what did she do?
“I went to my power users and asked them if they'd feel comfortable advocating for Gong to the new leadership.
They said yes.
Suddenly, instead of having one champion, I had dozens.
It still took a while to close the deal, but with some elbow grease and internal support, we got it across the finish line.”
The lesson? Have not just one advocate but many to get the best possible outcome.
9. Do $100 favors: Sam Nelson, SDR Leader at Outreach
While making calls and demos all day long can seem like a lonely job, sales is anything but a solitary profession.
Sam Nelson, SDR Leader at Outreach emphasizes this with his tip:
“Every time it is easy for you to do something that is worth at least $100 to someone else in your company, do it.
In sales you will notice a lot of opportunities to help a co-worker out and make them money through very little effort on your part. Some examples are sharing useful information, advice, or making an intro. Acting on these is a quick way to improve your happiness, the company culture, company value, and your own success.”
10. Keep growing your average deal size: Ryan Walsh, CEO at RepVue
Prior to leading RepVue, Ryan Walsh spent 17 years in sales — selling, leading sales teams, and mentoring sales professionals.
He believes that as SDRs advance in their sales careers, it is essential to look for roles where the average deal size is growing.
“You're not going to be able to break the $1M barrier closing a bunch of $3k annual deals. But that's also a gradual thing – if you're doing $3k deals now, look to parlay that into your next role where you're selling $15k deals, then $65k deals, etc.”
He adds:
“Another consideration is the sub-industry. We've seen some meaningful increases in compensation in the cybersecurity space over the past year. First of all, many of these opportunities do come with big deal sizes, (selling to the enterprise), and second, you just need to watch the news. A data breach or similar issue has huge consequences, and I think it's been prioritized for many large enterprises. Prioritization = budget. Budget = spend. Spend = commissions.”
11. Stand out from your competition: Dailius Wilson, CRO at Payble
Dailius Wilson is a sales professional as well as LinkedIn influencer most famous for posting one brand new tip around sales everyday. He has experimented with a wide variety of sales roles over the years, from advisor to entrepreneur and everything in between.
No wonder his LinkedIn is a goldmine of advice, especially for new SDRs.
In one of his posts, he stresses how crucial it is for SDRs to stand out from the crowd. And he suggests ten simple ways to do this.
.webp)
