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….

blog gif 1

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:

blog gif 2

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.


How I Turned an Icy Cold No into a Sizzling Yes

As a Customer Success Manager (or Inbox Ninja as we call it around here), the majority of my day focuses on taking a soft objection and transforming it into a warm lead for our clients. The other part of my day revolves around drinking coffee and catching Pokemon that sneak into our office – but that’s beside the point.

It’s become obvious to me that while choosing the right people to reach out to is important, identifying who has authority is the game-changer.

Let me give you an example.

One of my favorite clients creates customized experiences to help companies build more cohesive teams and better leaders (seriously cool stuff – ask me about it later if you’re interested). A few weeks ago, a Organizational Development Manager responded to one of my outreach emails on their behalf with a very stern “no” – it seems they were in a hectic transition phase and he did not have time for this right now.

What I wanted to say was…


But don’t worry. I kept my cool and assured him that I would reach out in a few months when they were through the transition.

Not even an hour later, an employee from the same company sent me an excited response that she’d love to chat with our company. Apparently, this is just what they needed! Woohoo!!

And guess who it was? The first respondent’s BOSS!

Boom. Roasted.

Long story short: my client had the meeting, closed the deal, and we all lived happily ever after. We weren’t discouraged by a no that really could’ve meant “I’m in the middle of something” or “I haven’t had my coffee” (which are both totally reasonable).

Three Takeaways:   

  1. Reach out to more than one contact: One person seldom has all the say in a decision to bring on a new vendor. Share information with people on different teams that would be impacted by the service you provide. Make sure you cover various departments that make sense and a variety of levels of employees.

  2. Don’t give up: The first response will probably be a “no”. That’s just life, ya know? But that doesn’t mean one of the other several people you reached out to won’t see exactly what they need in your outreach. Trust the process.

  3. Always be respectful: Please don’t use this post as permission to spam every employee at your dream company with the same email. Targeting is key. It’s also vital to acknowledge and comply with a “Please take our team off your outreach.” We’re not trying to make any enemies here – only give the right people a chance to say yes.

I hope this gives all you hard-working sales warriors some inspiration today. I’m rooting for you!

Keep Calm and Ninja On,



3 Ways To Earn Your Prospects’ Attention

How many emails have you gotten that look like this?

Hey Mark R!

I think my company can help LeadUp, LLC reach its goals this year. Because you are a Co-founder, I thought you might be the one with LeadUp, LLC’s budget for my company’s services!

Let’s chat Friday or Monday to see how much of LeadUp, LLC’s budget I can wrestle away from you, Mark R!



As you’re probably aware, the template used looked something like this:

“Hey {{first_name}}!

I think my company can help {{company}} reach its goals this year. Because you are a {{title}}, I thought you might be the one with {{company}}’s budget for my company’s services!

Let’s chat {{1_business_day_from_now}} or {{2_business_days_from_now}} to see how much of {{company}}’s budget I can wrestle away from you, {{first_name}}!


There are more platforms and tools available to help sales reps scale outreach efforts than ever before (Salesloft,, Replyapp), and these new sales super-powers should be used for good! When abused, however, it also creates email cacophony and it’s hard to cut through the noise when it’s already deafening.

Although sales people still face plenty of challenges related to Ideal Customer Profile creation and Buyer Persona segmentation, it’s a safe assumption that decision-makers are receiving more emails than ever, with {{dynamic_tags}} intended to add “personalization” to otherwise generic offers with bland calls to action.

The Cure For Poor Outreach

Over the last year, we’ve seen it all, made lots of mistakes, learned, and evolved. Here are three recommendations for delivering relevance with every outbound communication.

Educate Don’t Inundate

Our team’s thinking is constantly evolving (ideally at a pace just ahead of our clients’ needs!) and has recently been impacted by thought leadership from Jacco van der Kooij. I highly recommend any organization spend the $60-90 on his book Blueprints for a Saas Sales Organization.

However you approach prospects (eg: email, phone calls, social touches, content marketing, or any combination), prospect communication isn’t about you. Through trial and error, we’ve landed on an 80:20 ratio of targeted research and understanding of a prospect’s need paired with shared content and a request for a call where we offer to share helpful insights based on our similar client experience.

Our goal is to attract prospects that will benefit from our insights. These are surely the most likely to convert into customers, but modern sales conversions operate on the prospect’s timeline and are delivered to the best educators rather than traditional closers.

Do Your Homework

One of the more successful shifts our team has made for our clients and for our own outreach relates to the qualification process.

We admittedly backed into this finding, but our early process included standard discovery call questions related to identifying our prospects’ ideal customers, targeted buyer personas, value proposition, etc. We found, however, that despite a strong outline for guiding prospects through this call path to ascertain mutual fit, we came into calls underprepared to aggressively qualify mutual fit and educate adequately.

Our evolved process involves more homework in both outreach and qualification stages. Rather than following a standard script and forcing our AE’s to improvise on discovery calls, they are required to prepare the following:

  • Identify prospect’s value proposition
  • Find 2-3 logos or case studies from their website
  • Create example scenarios based on research where our process could uncover more of the same types of clients

This process accomplishes all of the tactical advantages of a discovery call sheet. You cannot make an educated guess on a prospect’s value proposition if you haven’t visited their website, read their “About” section, or looked through case studies and client logos that they want visitors to see. Thinking through an applied scenario or two forces AE’s to both ask themselves obvious questions and ask prospects more thoughtful questions once on the actual call.

When forced to push beyond the tactics, however, you create real value for prospects. AE’s are always looking to be viewed as strategic resources, but so few actually accomplish this. With AE’s doing the tactical homework and thinking about strategic alignment (via a standard framework), they are much more likely to deliver a valuable thirty minutes to a prospect and receive the first call when it’s time to make a purchase.

Lead With Process

We created LeadUp based on a fundamental assumption:

“A poor process executed consistently beats a brilliant idea with no follow through – always.”

Early on, we adopted what we’ve termed an assumption-based model of outreach. By targeting companies that fit an ideal customer profile (ICP) and segmenting buyer personas (BP’s), well-written messages are more likely to find prospects compelled to act on a good value proposition and a strong call-to-action.

We have learned, however, that a research-based model of outreach that is surrounded with insights is a much stronger process. Similar to the discovery call adaptation that we implemented internally, we shifted resources to deliver relevant insights to targeted people rather than conducting outreach based on broad assumptions.

People implicitly recognize that current process is a reflection of future process (or lack of process). In a sales context, if the handoff from an SDR to the AE is clunky or uncomfortable, it’s reasonable to assume implementation will also be clunky. Conversely, beginning a conversation based on a process of research and delivering insights sets the table for a partnership of shared insights and continuous improvement.

I hope this is helpful as your own sales process evolves. What immediately jumps out as aligned with your team’s work? Where do you disagree?

If you like this post, please let us know and share your experience in the comments! I look forward to learning from you.