In It to Win It

This blog marks the start of a new sales career: my own.  I’m on the brink of stepping out into the real world, and if there’s anything I’ve learned over the last four years at Emory University, it’s that I thrive in the midst of competition and pressure. Sales seemed like the natural career choice.

Just to give you an idea of how competitive I can get, during my first tennis season playing at Emory, before stepping foot on the court, I would always turn to my teammates and say with a smirk, “I’ll run a suicide for every game I lose.”  I was easily the cockiest girl around, some might even have called me obnoxious – who can blame them? But for me, there’s no such thing as being too competitive.  Over the next three years, my team went on to win two national championships, and I became a 5 time all-american: a testament to my competitiveness and hard work far more than my athleticism, trust me.

When people ask me whether or not I enjoy playing tennis, I’m always unsure about how to answer the question.  I do know two things; I’m competitive and I work hard.  I am driven by hearing somebody say, “You can’t do that,” As soon as I hear those words, I work my ass off to accomplish ten times what they said I couldn’t.  I want to be in sales because I want to feel that rush – the rush of proving that I can accomplish whatever anyone throws at me, over and over and over again.

I might be obsessed, but we’ve all got our kinks.  I’m going to channel that fixation the most productive way I can think of: starting here, at my sales development internship with LeadUp.  Hey, if my passion is winning, I might as well jump into a career that rewards winners.

I have no formal experience or education in business; I am not an authority on the matter of sales, and I’m not pretending to be.  I’m just a girl who hates losing more than anything else in the world.  So, why would anyone care what I think?  Because there’s always more you can do; I’m going to find that extra bit it takes to win, and I’m going to build on it.  If you’re looking to see what it takes to get to the top when starting from the bottom and build with me along the way, look no further.  Sales development, meet your new Yoda-in-training.

I’ll be using this blog as both an outlet and a resource for myself and for whoever wants to be part of my journey.  I’ll be sharing my successes and my failures, my favorite resources and experiences, with some sarcasm along the way.  If anybody has any recommendations for books, blogs, or any sources that will help me improve and get some early wins, I’m all ears.


First Month, First Lesson

I started my job at LeadUp exactly four weeks ago. During that time, I’ve learned a ton. But most of all, I’ve learned that there is so much out there that I have yet to learn…stay with me here.

This idea comes from a story a great mentor once shared–I’m going to call it “The Circle Principle.” Imagine you draw a circle in the middle of a white board. Everything inside that circle represents what you know, and everything outside of the circle represents all of the knowledge and wisdom in the world that you don’t know. As you gain more knowledge, your circle grows, absorbing more and more from the surrounding empty space on the board. But as your circle expands, so does its circumference. Therefore, you are touching more of the “unknowns;” you “know” more that isn’t know. Essentially, the more you know, the more aware you are of everything you do not know.

Four weeks ago, I stepped into an apartment on the beltline in Atlanta, but I also walked right out of my existing circle and into the blank space on the board–attempting to stay above water as I waded through all that I didn’t know.

At first, it very overwhelming. With no sales background whatsoever, I needed to learn the process and the game in a matter of days. Thankfully, the start-up culture is a fast-paced one, and I listened and observed until I could safely float. Every day I come in, I learn more, which builds my ability to navigate everything on my own.

Over the next few weeks, I’m going to take you through a few of the things that have found new residence inside my circle on the whiteboard. The first, and maybe one of the most important, is this: getting to the point.

My job title is the “LeadUp Content Strategist,” meaning that my main duty is to create email campaigns for our clients to send out to cold prospects in the hopes that one–or preferably many–will bite.

That means that I need to be concise and purposeful with every word I choose to place on someone’s screen. Because in all honesty, each of those words represents a millisecond I have taken from that person’s day. They might not need what I am offering and they definitely do not owe me any of their time. Therefore, it is essential that I use their time wisely.

Even so, it’s very hard for me as a writer to resist crafting perfectly-worded and clever emails that I spend hours revising. I want to make my words perfect, even if someone is only going to spend two seconds on them before sending them to the trash bin.  

But those types of emails, the ones that are laboriously crafted to appear conversational, don’t work. Trust me. A better strategy–strap in, this one is pretty crazy–is to only give yourself roughly 30 minutes to write an email chain….

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I know, I know, it’s crazy. But don’t look at me like that, anonymous reader! You’re scaring me.  

For my job, my time is much better spent getting to know the clients I am representing, rather than laboring over the placement of words and commas in the messages that represent them. Once I know the client, I can portray their key messages with ease and swiftness.

So I’ve got my first priority: getting to know the company I’m representing. The very close second to that priority is getting to know the people I will be reaching out to. But when you’re sending emails to around 800 people/month/client, that is nearly impossible–except that it isn’t.

Rather than learn every detail about Sue from HR’s life, I am going to spend a significant amount of time learning what HR professionals care about. What motivates them? What common struggles do they have? What humor and tone will they identify with? Once I know that information as well as I know the company I am representing, then I should only need 30 minutes to write a few very straight-forward emails that will show Sue that I can help her with this really great product/service. Because meanwhile, this is what Sue is thinking:

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Which brings me to my next point (thanks for the handoff, Sue): prioritizing information. Choosing which points are the most important to hit and presenting them so that they are easily digestible is no simple task. Thankfully, there is another lesson I’ve gained from years of writing (s/o to my mentor once again for giving me this wisdom) that always helps to put what is most important into perspective. It is a very simple principle that, quite honestly, demonstrated to me why I should take this job in the first place. I knew I could be successful in my role because I have the following knowledge:

To make the audience the hero of the story.

With that in mind, the sales process completely changes. I would tell you all about it now, but I want to keep you in suspense for next week where I will delve much deeper into this principle. For now, congratulations! You made it to the end of my first blog post. And I’ve made it through my first month of work. Let’s celebrate together by continuing this blog reader-writer relationship for a little while longer :). Comment below and maybe we can expand each other’s Circle of Knowledge by sharing ideas.


Why SDR’s Make Bad SDR’s

In the modern sales organization, the SDR is the lynchpin of the entire operation. SDR’s enable account executives to focus on nuanced conversations with qualified prospects at targeted companies, and ultimately win complex deals more quickly.

The SDR also coordinates collaboration between sales and marketing. Marketing strategy informs the Ideal Customer Profile and Buyer Persona segmentation, and it is eventually re-informed based on outcomes provided by SDR activities. If the alignment of sales and marketing isn’t accurately translated and communicated to the SDR, sales and marketing efforts suffer.

Let’s start with the qualities that sales organizations look for in a great SDR. I’ve broken it down into four distinct areas:

  1. High degree of empathy (attentiveness to customer needs)
  2. Strong written and verbal communication skills
  3. Curiosity – ability to ask good questions and interact thoughtfully with decision makers
  4. Ability to create targeted lists of companies and contacts

SDR’s put these characteristics into practice by prospecting the right companies and buyers, writing compelling outreach messages, keeping a steady cadence of cold calls, and creating a consistent multi-channel strategy–all the while constantly testing & improving on this process.

For SDR’s to excel, however, there are two opposing forces at work.

Companies like the ability to vet young sales candidates by grinding them through the SDR track to prepare them for success as an AE. Unfortunately, future sales all-stars don’t necessarily have the skills to be strong SDRs, nor do SDRs prove their mettle to become AEs by slogging through prospecting lists and cold calls.

These characteristics are the skills required to be successful in sales development. The only reason not to break them out completely would be if you could find those skills consistently in the same type of person. And this simply isn’t the case.

Modern sales has improved, but hasn’t caught up to the modern buyer. Further specialization is required.

Billy Beane is most famous for his “Moneyball” approach to building the Oakland A’s baseball teams as General Manager, where he values the specialized contributions each player has as they relate to scoring or preventing runs scored (how games are won and lost in baseball).  As a player himself, Beane was considered a “5-tool prospect.” He could hit for average, hit for power, run the bases, throw well, and play the field, but his career ultimately didn’t pan out. From the front office, he went against conventional preference for finding the perfect player and brought in the best collection of skills that could win games – which often came from multiple players who were independently flawed, but collectively perfectly complemented one another.

Sales is the same game. At most companies, SDR’s are expected to be just like that 5-tool player along their progression towards becoming an AE and eventually a sales leader. These players exist, and they usually become All-Stars. They are also anomalies. Championship teams are built by assembling role players to support their stars, and great modern sales organizations will find a competitive advantage by further specializing this critical SDR role.

To begin specializing the functions an SDR performs, I suggest mapping them against the characteristics laid out above:


Building out a function that exists purely to usher prospects through onboarding into customer success is critical. This role plays quarterback for the other functions below, fully understanding the ideal customer profile, buyer personas, KPI’s, and tasked with pulling any team member below onto a call throughout the process to ensure success.

We built this function into the very center of our process at LeadUp. They calls the plays and make sure that clients’ needs are addressed proactively. Empathy fuels the engine rather than hunger to sell more business. The empathetic quarterback has a long view of the relationship from the outset and makes sure that shortcuts aren’t taken just to make sure a contract gets signed.

Writing Skills

If you can’t write in a modern sales organization, you are working with borrowed time. As communication moves across multiple channels, sales organizations that value and hire for writing as a skill will separate themselves.

At LeadUp we love to hire English and Journalism majors. Not only can they write, but they have usually gone to great lengths to get a story in the past. Their passion reminds me a lot of great salespeople, but the motivation of a writer is often less financial and more out of desire for a great story, or to get to the truth.

Client Curiosity

This lines up with why I love writers, but client curiosity typically looks like someone who constantly tinkers. A good fit might look like someone who obsessed over baseball as a child, got into surfing in their teens, swore they’d take over Wall Street in their early 20’s, then ended up at an NGO after a stint in the Peace Corps. Everything is interesting until 80% of mastery/understanding is reached. Then it’s time to be curious in another direction.

Jacks-of-all-trades fit well in this role because they are naturally curious, can be very focused, but also need to be constantly learning in order to stay productive. Salespeople have plenty of room for this characteristic, but it’s often buried in those too busy for natural curiosity to flourish and help the team.

Data Strategy

The full SDR picture wouldn’t be complete without targeted, account-based prospecting. In the modern SDR’s day, this is required in order to meet other outcome metrics, but can become a bit of a drudgery if they are looking to progress towards becoming an AE.

The Data Strategist has two complementary strengths. This person is very attentive to detail and enjoys supporting a team without the need to be in the spotlight. We discovered this person on our team because they were the one who brought a kitchen scale to measure out coffee beans. The sales team was pouring bags of coffee into the coffee maker without a second thought, while LeadUp’s future Data Strategist made sure that exactly 17 grams of beans were portioned, ground at the medium-fine setting, and spent no more than thirty seconds in 195-205 degree water, before gently coaxing it through the Aeropress into her mug.

In addition to this stark contrast in attention to detail for process, she appreciates the generally underappreciated nuance between coffee beans. Is it Arabica or Robusta? Is it grown in Africa or Central America? A typical sales person only wants to know whether the coffee is leaded or unleaded–caf or decaf. This penchant to dig into underappreciated nuance falls outside of the limelight, but is critical for a successful targeted data strategy.

Each organization has different hiring priorities and means of approaching the SDR position. As the role grows in prominence and organizations mature their understanding and practice of modern sales, I suggest looking at these four additional areas of specialization. Ask how  these specialties can be applied now and built into future plans in order to create a sales machine capable of scalable human interaction.

If you like this post, please click the thumbs up below and share your experience in the comments! If you disagree – let’s talk about it. If you agree – tell me why!