Breaking Through (Part One): My (humbling-as-heck) lesson about inbound sales communication

Recently, I posted a joke about a trend I’d been seeing a lot on LinkedIn and in my email inbox. I wrote:

“Pro tip: if you’re hoping I’ll reply to your cold outreach email or linkedin message, maybe don’t start your message with ‘Dear Benton’”

Almost immediately, things got weird. Typically, a post like this might get a few likes, and a few hundred views. I didn’t use a hashtag, nor did I tag anyone. In other words, I wasn’t trying to get a bunch of views or create some sort of viral thing. I was just feeling sarcastic after receiving a bunch of impersonal, (I felt) poorly written sales pitches. Most of these came through LinkedIn, but plenty have guessed my email address and hit my inbox. Bad form, I thought. I’d had enough. I wasn’t prepared for what happened next.

That post, to date, has received over 15,000 views and has dozens of comments. Many responses were sympathetic – others who felt like these were mass-communicated, spaghetti-on-the-wall spam tactics. But a few folks pushed back, citing cultural differences and pointing out that my snark might be misguided. Others questioned my logic. “So what if it’s a mass communication, or a poorly written note? Aren’t you still limiting yourself from opportunity by not responding?” (I’m paraphrasing).

Whoa. This is some provocative stuff – these folks make some pretty good points. Many of us work in industries that are fairly agnostic to borders – is my bias toward a certain style, format or salutation actually holding me back? Am I being so snooty that I’m missing out on good opportunities? Worse yet, could this be an unintentional form of discrimination? I decided that I need to think more seriously about this.

I take this kind of thing personally. Introspection isn’t always easy. I hate discrimination and I despise unfairly biased thinking. I absolutely shudder to think I might be guilty of either. From a purely business perspective, if we’re missing opportunities for any reason, I had better get to the bottom it. I decided to conduct a little experiment.

I chose two messages that I wouldn’t normally entertain. Instead of ignoring them, I wrote a thoughtful response to each. The first was an inbound email, the seventh in a series of uninvited communications from an overseas firm looking to sell us on their services. The second was a LinkedIn message from a firm that builds explainer videos (the example they sent was about stem cells!). In each case I responded, saying that I typically don’t reply to such communications, but that I’d be happy to learn more. To the overseas firm, I offered a 15-minute call to learn about their product. To the LinkedIn message, I wrote that I’d received dozens of similar communications, and that I’d be interested in knowing what sets the sender’s firm apart, and also how they think they could help us. Here goes nothing, I thought. The results confirmed my hunch that I can and should do a better job of exploring inbound opportunities. Much, much better.

The overseas firm blew me away. No joke. The 15 minute call went 45 minutes. Then, I asked my partner to review it – he called it a ‘no brainer.’ He’s right – it’s got the potential to help our team in a number of ways. While I still maintain that they approached me in the wrong way, we’re definitely going to buy their product.

The firm that builds explainer videos fared worse. I got a canned message back with a list of giant enterprise examples (that have no reasonable connection to who we are or what we do). The sender suggested I talk to someone else in her organization if I was interested. Not impressed.

There’s a lot to learn, here. First off, I’m clearly guilty of not thinking deeply enough. I valued form over function – mostly due to being busy. Maybe that sounds like a tough pill to swallow, but I’m happy to have learned my lesson. We’re better for this humbling experience.

But what about the senders? Wouldn’t they benefit from some tweaking to improve their own efforts? I think so. This problem won’t be solved by expecting folks to look in the mirror and become more open to inbound sales pitches (though as I’ve experienced, we all should). There’s always room to improve, and for any business development or sales professional looking to break through the noise, there are better ways to get the prospect’s attention.

I’m going to tackle this topic in part 2, next week. Stay tuned!

Join Us At InsureTech Connect in Las Vegas!

Earlier today, we announced that we will be partnering with InsureTech Connect as part of their annual conference in Las Vegas. The four-hour, pre-conference program will be available exclusively to conference attendees, and will feature content contributions from throughout the insurance technology ecosystem and insurance-adjacent industries. For us, this is big news on a couple important fronts. Read on!

First, I’ve known the conference’s founder, Jay Weintraub, since my first month in the performance marketing space. In many ways, his ideas have provided a platform for my career to flourish. Over time, I’ve come to know Jay as a dear friend. Partnering with him – and the entire InsureTech Connect team – is a tremendous honor for us. If you’re reading this, Jay and team, thank you.

Beyond the personal stuff, we’re excited about this because it perfectly aligns with who we are and what we do. We power partnerships for firms across the insurance ecosystem, many of which are highly focused on emerging technologies. Very quickly, InsureTech Connect has become one of the insurance industry’s most innovative and important events, so being chosen to participate is validation of our own momentum.

What Attendees Should Expect:
If you haven’t attended one of our events in the past, it’s important to adjust your expectations, as this is not a typical session. Here’s what you can expect from this workshop:

  1. This will be entirely focused on thought leadership and education – it will absolutely never be about a sales pitch.
  2. All programming and content will come from industry thought leaders – WorkBook6’s job is to recruit great contributors and facilitate fantastic content.
  3. The focus will be entirely on growth-oriented partnerships.
  4. Space is very much limited. We have capacity for roughly 75 attendees (our last event attracted nearly 200). Get there early and be sure to reference the below information in your travel planning.

Where, When and How:
If you’ve already registered for InsureTech Connect, you’re good to go – just be sure to be at the MGM Grand on Monday, October 1 in time for the event. If you haven’t registered, we’ve provided a link with a discount for you, below.

MGM Grand – Rooms 204 & 205
October 1, 2018
1:00pm – 5:00pm

Registration Link:



10 Things You Didn’t Know About Us

By JT Benton

I get to tell our story quite a bit. But, because I try to listen hard and pair my presentation to the things I’ve learned about the folks I’m talking to, I don’t always tell it the same way. After just about every call or meeting, I’m left wishing I’d mentioned some other stuff. With this in mind, I thought it would be fun to put a little list together that contains some of the more passed over details about WorkBook6. And so, I proudly present 10 things you likely didn’t know about WorkBook6. Hope you enjoy!

  1. The story behind our name isn’t all that creative, but it is funny (at least to us). I was working on the business model many years ago and when I saved my work, I noticed that the suggested file name was workbook6.xslx. I thought it was catchy, and since I didn’t have a crystal clear vision of the business, yet, I liked how vague it was. Further, a mentor of mine at the time was in the process of a costly rebrand; his advice was to stay very high level and leave room for expansion. So, we went with it.
  2. While I’ve been excited about this concept for a long time, I didn’t have the guts to actually start the business until 2016. Why? I finally saw the opportunity had scale. And, I had to do it. My last gig (CRO for a national insurance firm) was really hard on my family. When that began to unwind, I felt like I had to take better control of my time, travel, and team. I started working on WorkBook6 the next day.
  3. Our first client is still with us. I pitched the idea over lunch and later that afternoon, we had our first yes – a very well-known US financial institution! What’s better, still, is that the decision maker has become a very close friend.
  4. We have never raised capital. Every hire, technology investment, rent check, insurance premium and company lunch has been funded by our growth. This hasn’t been easy, and the hard work is far from over, but I wouldn’t change a thing. This independence makes it easy to know who we’re accountable to – every dime in our accounts came from a client.
  5. Our vacation policy is worth smiling about. It is as follows:
    • – Do great work always.
    • – Make sure your colleagues never suffer from your absence (or your presence, for that matter).
    • – Otherwise, take as much time away as you’d like – just make sure the work stays excellent.
  6. While we’re headquartered in Tempe, Az, we have folks on each coast (Boston and Santa Barbara) as well as Colorado.
  7. We’re not a lead generation business, nor are we an ad agency. We’re 100 percent focused on forging partnerships on behalf of our clients. (So if you ask me how much the leads are, I’m gonna make a funny face.)
  8. We’re entirely industry and location agnostic. WorkBook6 has clients in over a dozen vertical markets and we have represented companies in the US, Europe, Middle East, Africa and Australia.
  9. While we are a service-oriented business, we’re very much tech-enabled. When we discovered there wasn’t a CRM platform that worked off the shelf, we decided to build our own. While we don’t brag about it enough, WorkBook6 operates on its own, completely proprietary CRM system, which we call
  10. Finally, we’re a special snowflake. Seriously, to the best of our knowledge, there isn’t another company that does what we do. I’m not sure if that means we’re crazy or brilliant, but either way, I love that we’re unique.
Let’s Connect!