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.


3 Reasons To Delete Cold Emails

I was on a call with a prospect recently who was asking about our team’s approach to setting appointments and what success looks like for our clients. When I clarified that we rely primarily on email to drive appointments, he paused as though he had something to get off his chest.

“Mark, I delete cold emails. I don’t have time to read them unless they’re offering something that will clearly help my business.”

In my mind, I responded as though it were the twist in an M. Night Shyamalan movie – the classic “I see dead people” moment.

“Listen, Fred {{dramatic pause}}, I delete cold emails too.”


I know what you’re thinking – sounds hypocritical, right? This guy starts a company and works with a team whose primary aim is to procure meetings for clients via cold-email, yet still deletes cold emails. Doesn’t add up.

Don’t get me wrong, we save the really bad ones. We have a “Wall Of Shame” that keeps us humble and reminds us to be courteous and respectful with each interaction. The truth is, however, it’s easier than ever to over-communicate with prospects and it’s crucial to avoid these classic mistakes if you want to rise above the noise and make email a successful part of your sales process.

We’ve put together three reasons to keep deleting those cold emails:

Not Relevant To Your Business

How many messages have you received where a catchy subject line got you to open an email, only to be disappointed by an irrelevant message? I’ve never needed pipe fittings nor do I expect to need them in the future – how did I end up on that list?

There are many ways your business ends up on prospecting lists, but the primary offense you should aim to avoid is prospecting companies outside of your ideal customer profile (ICP). The first filter towards qualification is targeting companies that are most likely to find value in your service. We recommend revisiting your own ICP definitions quarterly to ensure every salesperson has a clear understanding of who derives the most value working with you.

If that email in your inbox isn’t something your business could use – unsubscribe and delete – guilt-free.

Not Relevant To Your Role

Assuming your title reflects your role and responsibilities, it’s aggravating to receive an email that could have been sent to anyone.

Receiving an email that isn’t relevant to what I do or could be relevant to anyone reflects a poor process of identification. I’ll give a pass to those prospecting people with ambiguous titles. In a previous role I had a VP title that was conferred upon me as I headed off to attend a trade show. It didn’t reflect any formal management or budget authority but those who prospected me couldn’t have known that prior to a conversation.

Relevance can be improved, in general, by taking a more thoughtful approach to buyer persona (BP) segmentation and tailoring messages to address the strategic or tactical pain points of those BP’s with a proposed solution.

If you are an engineer and the email sender asks for an hour to discuss your sales process – gleefully unsubscribe and delete.

Unreasonable Ask In The Message

Cold emails rarely provide an offer with enough replacement value to be compelling.

For example, a salesperson churning through a prospecting quota may ask for an hour of your time to discuss X. As a reasonable opportunist, you scratch your head and consider the value of that hour of your time, the opportunity cost involved in offering it to the sender, and the potential upside of a meaningful interaction.

Time is your non-renewable resource to guard carefully. Why give it away to an unsolicited emailer who parachuted into your inbox unannounced? You won’t unless their offer conveys a future value concisely that aligns or uncovers an existing need.

If they aren’t offering more value than they are asking from you – unsubscribe and delete without a second thought.

Tying it All Together

At LeadUp, we believe honesty and transparency are the best policies to drive cold email success. Start with a clear ICP, then prospect companies in that ICP – simple. Next, define your BP’s and paint vivid pictures of where those personas care deeply. Finally, create a message that provides value and suggests you would be a partner worth giving a shot!

The Top 5 Things Your Sales Reps Should Do (Instead of Prospecting)

One of the most common objections I hear when discussing our lead generation services with a prospect is:

“We already have someone doing that, and frankly, he/she’s not that busy.” _Most VP’s of Sales

Anyone from the CSO to the Sales Manager might assume that if their sales reps are unburdened from two hours of prospecting and targeting clients, there’s a good chance that rep will use the time to go to the gym, find an early happy hour or walk the dog. Therein lies a clear problem.

To further compound this challenge, in the past, a successful salesperson was and “all-’rounder”. They were adept at identifying companies to target, people to reach out to at those companies, mutually qualifying readiness and interest from prospects, and most importantly, closing new business. Depending on the size of the business, they could also be expected to further penetrate and grow existing accounts.

Advancing technology and role specialization is changing the game, allowing for companies to hire or outsource specifically for each stage of the sales process, and providing the chance to hire closers to close with lower risk all around.

I’ve put together a list of The Top 5 Things Your Reps Should Do (Instead of Prospecting):

Deliver more demos and/or qualified meetings

This may be the most compelling of the all of the reasons to take daily prospecting off of your reps’ to-do lists. Let’s just say a discovery call or follow up appointment takes ~30 minutes. Two hours a day would give your reps the chance to complete 4 more new client discovery calls or follow ups. That’s a potential increase of 20 per week or 80 per month, per rep.

I realize that’s fuzzy math (sometimes called “sales math”) but imagine the impact half or a quarter of that increased productivity could have on your business, spread across multiple reps. That increase isn’t accretive… it’s staggering.

Spend time with existing customers

By visiting with clients, several things happen. Firstly, relationships strengthen. The more we get to know the people we sell to and buy from, the more genuine interactions become. Mutual affinity and investment solidifies desire to continue working together.

Secondly, you have the chance to learn more about what’s really going on. This is fundamental, but how many accounts do you have where you don’t fully understand the economic and strategic driver that keeps your client doing business with you? Probably more than you care to admit. How can you continue to contract business via renewals or additional services without intimately understanding what challenges you are solving?

These are questions that need answers, and you reps can get the answers more readily by developing stronger relationships with more decisions makers, mobilizers and insiders at your clients.

Strategically map relationships and buying dynamics at target and/or existing accounts

Without specialization, there is clear mental opportunity-cost to your reps’ focus. If you expect your teams to perform a combination of growing targeted accounts, prospecting into white space/green pastures, and converting warm leads into new contracts, you are asking for trouble.

A combination of your reps’ individual strengths and the structure of your incentive compensation plan will typically determine what areas are naturally emphasized and which fall apart. In addition to designing compensation to align with each role, an easy way to put time back into your reps’ calendars for strategic activities is to remove the tactical burden of prospecting and cold-outreach.

Join your internal “Upsell Power Hour”

I’ve written about our internal dedication to Prospecting Power Hour at LeadUp. We celebrate and emphasize prospecting internally because it is sacred to our business and to our clients’ success.

Once your business has either specialized the role of prospecting or outsourced it to a partner like LeadUp, you can implement a replacement activity such as “Upsell Power Hour”.

You rely on existing accounts for recurring revenue and they often represent the best growth opportunities for existing services. You already have key relationships with decision makers and have delivered consistently so that mobilizers and insiders trust you. You’ve made everyone look good and it’s in their best interest to find more to do with you rather than seek out new partners.

Why not spend time on a daily or weekly basis elevating this activity and measuring the ROI over a three-month period? You could even consider offering bonuses above and beyond standard commissions based on production from this daily/weekly time. It will likely become your most profitable block of time and well worth creating momentum and excitement internally.

Train and mentor other team members

With more time available, you should look to increase the development responsibilities of your individual contributors. Making development the responsibility of everyone in the company, regardless of title increases accountability for results in addition to accelerating the development of newer team members.

One of the greatest shortcomings seen among high-performing sales reps is the inability to transfer that same level of performance to sales management. By conferring developmental responsibilities sooner, you create a low-risk means by which to assess capability and readiness rather than promoting your employees into their highest level of incompetence unknowingly.

About LeadUp

Services like LeadUp offer to unburden companies from top-of-the-funnel activities like prospecting target companies, finding the right buyers at those companies, sourcing validated contact information, and setting appointments with qualified buyers. We give critical time back to your reps and create a steady flow of qualified buyers arriving on your doorstep.


Millennials Should Sell: Part 3

I’ve articulated that sales is often marginalized (sometimes rightly) but also serves as a powerful corporate development tool when done intentionally.

An entire post could be written on what the hiring manager on the other side of the table wants to see (and it has). Here I will touch on several benefits of beginning a career in sales to the recent graduate. Don’t be surprised if a tinge of regret emanates from the page and this post reads like an open-letter to a much younger version of myself.

Feeds natural curiosity:

You, the recent graduate, exude confidence, idealism and curiosity. What better time to take on a structure and trajectory that harnesses your natural curiosity? In sales, you are immediately exposed to a range of company sizes, cultures, industries and functions. Behind the veil of job titles and corporate bureaucracy, you will work with real buyers who are actual people. Do you like what you see in them? Sales is a great (paid) way to evaluate.

Develops coveted leadership skills:

Getting from lead generation to signed contract requires an enormous amount of cross-functional finesse. Early in my career, I sold health benefits to large corporations. An average deal required that I coordinate internally with data analysts, underwriters, actuaries, proposal writers, countless subject matter experts and my sales leadership. Ultimately, I was the one on the hook to get the deal across the finish line and was compensated (or not) accordingly.

Getting alignment and cooperation from a network where you have no hierarchical authority is a skill companies are looking for at their highest levels of leadership. Those who figure it out accelerate past their peers. How does that sound?

Quantifies contribution:

An age-old method to filter sales candidates is asking for your most recent W2 statements. The thinking is that a sales person should either make a substantial amount (varies by industry) consistently if he is successful, or should make an escalating amount each year as he is given greater responsibility and is successful.

As much as this tactic makes my skin crawl (it is the professional equivalent of an arm wrestling match), there is a reason sales managers use it – a successful sales rep can show proof of success on his pay stub. In sales, we have a scoreboard. Our output is binary. Did we produce revenue or not? Try asking an interviewee for a human resources position to show you their last three pay stubs…

Forced to improve communication skills:

By constantly interacting with customers, you are always performing. Every cold email, cold call, LinkedIn interaction, demo, face to face meeting, internal strategy meeting and sales round table gives you the chance to practice communicating clearly and effectively.

Although any role includes elements of sales, client-facing selling is particularly valuable for developing communication skills because you receive instantaneous feedback. Not only do you find out whether your good/service appeals to your prospect, but you find out whether you made any sense at all. Sometimes clients are candid and tell you a pitch is horrible, but more often a pregnant pause or squint of the eye sends just as valuable a message.

When you’re asking for someone’s money, they tend to be honest with you.

Control earning potential:

As the saying goes, in sales you eat what you kill. Whatever sales role you assume, you have a portion of compensation that is variable, tied to KPI’s such as customer retention or acquisition, revenue, profitability, etc.

As a former collegiate wrestler, I wasn’t yoked to under performers when I stepped onto the mat to compete. It was important to be pushed in training by good teammates and to chase team goals, but between the competitive lines, it was me versus my opponent.

Sales provides the same type of individual reward. Rather than punching a time clock, you choose an achievement mentality that is rewarded with measured wins and losses. If you win more, you also earn more. Sometimes a lot more.

In what other ways is sales a good career gateway? What caveats would you include?

Millennials Should Sell: Part 2

In my previous post, I suggested that beginning a career in sales serves both the companies hiring talent and the talent being hired. I will tackle the company’s perspective in this piece.

As the millennial workforce continues to cry out for development plans over health benefits, creating more specialized sales roles offers companies the chance to create a dynamic and structured career path that might just be attractive enough for young employees to outlive the 18-36 month expiration dates they carry along on their career passports.

At a very general level, a simple sales career progression in a SaaS company could look like this:

Inbound lead qualifier => Outbound prospector => Outbound lead generator => Inbound/outbound sales demo team => New business executive/Account executive => Senior new business executive/Account executive

This example has several trail spurs that could be spun off creating even more possibilities. The key takeaway is that creating multiple areas of specialization suits a company’s need to increase bench strength through internal development and retention.

1. Clear Development Plan:

Specific metrics to progress to the next stage can be attached to each of the roles suggested above. For example, if a new inbound lead qualifier passes 50+ qualified inbound leads to the inbound sales demo team each month for 3 consecutive months, he automatically gets promoted to become an outbound prospector. No ambiguity. When his manager sits down for a coaching review, the rep knows why he did or did not progress and control when he can expect another change. Just like in Monopoly, if you do not pass “GO” you do not collect $200. It’s simple.

Some new hires will not hit the necessary metrics. Once the criteria has been calibrated internally and talent acquisition has a clear employee persona to target, roughly 2 out of 3 hires should progress to the next role in the average period of time. In the example above, 2 of 3 new hires should move to the outbound prospecting team within 3 months of getting ramped up.

But what happens if they don’t?

2. Not Wired to Sell?

There will always be candidates who fit your company culturally and pass the assessment to begin in sales, but cannot perform. By hiring younger talent and measuring from the beginning, you position your company to redeploy good people away from sales roles into customer service, operations, marketing, or other areas that fit their skills and company needs.

This comes at a much lower opportunity cost than pursuing mid-career hires exclusively, cutting underperforming reps immediately, or worst of all, allowing marginal performers to slip through in perpetuity – yuck. Although hiring younger doesn’t spare you the pain of every mismatch, it gives you lateral and vertical flexibility to develop talent that fits your organizational culture.

3. Accountability/Ownership:

Every company owner would like employees to treat the company as if it were their own. By creating a culture where your people swipe corporate cards like real money, problem-solve with a view of commercial impact and generally making decisions with a full understanding of profitability and revenue creation, you largely circumvent the yoke of presenteeism.

We’ve all worked with empty-suits. My Texan friends refer to them as “big hat and no cattle”. No one wants to knowingly hire an empty suit. By using sales as a pipeline development tool, more of your young workers are directly exposed to customers and bear the positive stress of a quota. Any lessons learned in sales will not be soon forgotten as these employees migrate into other departments. The stress of meeting a quota and having objective measurements monthly, quarterly and annually gives each of us an owner’s mentality.

What other areas does it benefit a company to consider sales as a millennial development tool?

The Power of Enthusiasm

Most people watching Duke play Wisconsin in this year’s NCAA finals became acquainted with Grayson Allen for the first time. He didn’t play in two of Duke’s first eight games and saw more minutes on the bench than on the court for the majority of the season. In the NCAA Championship, the freshman scored sixteen points and was the clear emotional catalyst for the Blue Devils.

The most interesting aspect of Grayson Allen’s development this season (IMHO) is what Coach Mike Krzyzewski asked of him during their preseason one-on-one to discuss his role. Rather than discussing strategy or tactics, Coach K told Allen his role was to be “enthusiastic.”

Anyone who saw Duke clinch the NCAA Championship this year could see that not only did Allen develop as a player this season, but he took his role very seriously. He was the heartbeat of the team during a tenuous stretch in the second half where Duke found itself down by nine points. Allen was tenacious and above all else, enthusiastic.

Below are three reasons I value enthusiasm as highly as talent and intellect.

1. You can control it:

Some make the case that talent is more than pure natural ability; that it is the output of lots of hard work, involving a series of intentional choices to develop a specific skillset. I have no reason to disagree. But I still choose enthusiasm.

While talent takes a variable amount of time to develop, I can elect to be enthusiastic immediately and the effects are instantly noticeable once a 100mg dose of morning caffeine hits my bloodstream. (Before coffee, I can’t even spell “enthusiasm”).

How enthusiastic are you at home or work? What would change immediately if you focused your energy on being more enthusiastic?

2. Demonstrates buy-in:

Employees who are enthusiastic buy in to your mission. When you hit a rough quarter, you look to the enthusiastic leaders to right the ship. Without enthusiasm, all the talent in the world will not be motivated to make any progress. You know the old saying about adversity. It doesn’t build character, it reveals it. Enthusiasm gets you out of it.

What crisis are you in the midst of currently? How can you pour more enthusiasm into finding a solution?

3. Creates a lead domino:

The most compelling argument in favor of enthusiasm is that it is contagious. For anecdotal evidence, I am forced to look no further than my two oldest daughters. When either of them hear mention of an ice cream sandwich, pandemonium breaks out. Both of them go nuts.

The youngest doesn’t even like ice cream sandwiches. Nevertheless, when she sees her sister’s exuberance that ice cream sandwiches are in play, she matches pitch and volume. Things escalate quickly.

Are you surrounding yourself with enthusiastic friends? Do you value enthusiasm in the hiring process?

What are some other areas where you find enthusiasm valuable? Any good examples?