I posted recently about the importance to periodically check how a current role/ position fits into the greater journey – “Before Making Moves Based On Today’s Bad, Chart How All The Dots Align to A Path”. I took this to heart recently by reviewing my resume and updating my skills and experience. It’s made me aware of my career progression and my upcoming path as I head into my mid-30s. In short: optically, I’ve been rather stagnant.
Building a startup is incredibly hard work. Many startups do not come close to the type of success that is read about in the news or even the local startup digest. Entrepreneurship, though intrinsically rewarding, is not well-received professionally.
As I’ve had the great opportunities to lead sales at Body Boss Fitness, SalesWise, and SalesWise’s new product/ brand Burner Rocket, they’ve all been tough experiences to get through. Starting from virtually nothing and fighting to get scraps of the first 10 customers and then the next is rarely seen from the outside. The mind soaks up more information than what any “normal corporate” job may provide. However, it’s, in some ways, specialized. The bruises and cuts that I have felt by leading the charge for what a sales process may look like, what are the pieces of collateral that will help sell, how do we support our customers when we don’t even know the full metrics of what is working and what is not… those lessons are not always visible to the outside world. And yet, I know the incredible value that has been learned. I know the pains and the difficulties to get to where we are. I have good hypotheses for why we may not have grown at a faster clip, but from the outside, there’s little stock. Growing from 0-10 may not be as impressive as being a leader who hit the $2MM ARR quota from last year’s $1.5MM. Should that be?
Again, periodically looking through the portfolios of seemingly little accomplishments for early-stage opportunities, I can sense there’s a strain. There’s a pull and a fight between the desire to hop into a role where the hard work has mostly been done. Perhaps, there’s a need for an optimizer or a player to just “grow more”. It’s a struggle – to be a part of something so early that the chances of success are low. The challenges and rewards are greater. Or, do I take the easier route by following the path others have already trotted on before. In that way, perhaps I can have the requisite bullet points for others to note and say, “yes, he’s had that experience of hitting XX of quota”.
Being an entrepreneur and taking a real fight to creating something special isn’t always lauded. It’s rarely what folks are really looking for. But they’re the opportunities I’m looking for. It looks like I’m still on the right path.
One year ago, I announced I jumped full-time with a startup called SalesWise. It had been several years since I had worked for a company (April 2012, I left Chainalytics and the corporate/ consulting world). They say one year in consulting is like working seven years in “corporate” job. I’d say that’s more fitting to say from my one year at SalesWise, and hungry for more.
SalesWise is still an early-stage company. When I joined, I was the first business hire. It enabled me to get in on the ground, and start building out… well, everything – sales, marketing, customer success, and more.
A few lessons learned:
  • It’s been a lot harder. When I joined, I was thinking, “wow, the product is great! The two founders are experienced. The CEO has even started four with all four successful exits. This will be a rocket ship!” Not so much. Modern B2B sales is harder than most people think. Every new startup is a new company with, likely, a new idea. There are tools to make things easier, better equipped, but it’s still very, very hard to build a company.
  • I’m doing what I feared I would – keep wanting to do more. I joined the company because I felt I was starting to distrust others. I joined to help me trust working with others. But no matter what, I catch myself wanting to do more, so I don’t have to rely on others. I think to myself how can I learn to program some, just so I can help speed things up. It’s crazy. I’m already manhandling the other sides of the business. I want us to be successful, and I have this insatiable hunger to do more – to test, to deliver, to sell. I need to specialize on my side of the wall, and let others specialize where I don’t.
  • There are so many tools to help a company… and confuse. The number of SaaS tools available for companies is daunting. There are so many analytics programs, customer success tools, support apps, marketing platforms, etc. It’s a dizzying array of programs to help a company know everything that’s happening, and to keep the company buzzing. However, it can be too much. I have four screens around me – most split-screened so I can monitor everything. Is it too much? Maybe. The key is using each tool effectively for what it’s supposed to do.
  • A passionate, highly intelligent team members is more amazing. I didn’t meet everyone at the company before I joined. However, it’s been fascinating the personalities at the company. Each person is highly, highly intelligent – perhaps the smartest folks I’ve had the pleasure of working with. Most are very passionate about the direction of the company, and they truly own their areas of expertise. We have plenty of passionate debates during team lunches. They’re all healthy, and they give perspective to create the best approach.
  • Following a highly successful leader who is also very transparent and honest is… amazing.I can’t tell you how often I’ve been amazed at how my CEO has been open about our company’s direction and funding. He’s listened to everyone’s input, and though he may disagree at points, he hears us all out. He’s taken time to share his intentions while looking out for our own ownership stakes in the company, and he’s making decisions in the best interest of us, our customers, and our investors. There hasn’t been as much of explicit 1-on-1 mentoring with me, per se, but I’ve been absorbing everything just in everyday interactions. It’s been fascinating, refreshing, and hugely motivating.

When I started, we were launching a product for sales (reps and leaders). We had no customers. We pivoted a couple times last year before landing on our current direction. We’re now selling specifically for sales leadership. We have a dozen customers who are passionate about what we’re doing, and we’re seeing engagement numbers climb steadily. Our close rates are incredibly high at about 4 of 5 trials converting. We just raised $1.3M to build a repeatable customer acquisition process before cranking up the machine. We’ve hired several sales professionals, and are now in the market looking for a marketer. We’re building out the Business Relationship Intelligence category. It’s going to be an exciting next year.

This year has started off with a BANG, so I’m continuing this trend by announcing that I’ve excitedly accepted a position at Atlanta-based startup SalesWise!

Many thoughts running through my head… speaking of which, I’m officially the Head of Sales and Marketing… for a truly amazing company.

Let me rewind, and explain how this opportunity came to fruition…

For the last several years since Body Boss, I’ve consulted for several businesses (startups to $1B+ companies) doing business development, web and app development, product management, supply chain, and more. I didn’t have a clear idea of what my Next Great Move was going to be, but used consulting to network, learn, practice, and be inspired.
In October last year, with one of my consulting clients, I got to view a demo of new technology from an accomplished CEO and his cofounding CTO. I experienced an impressive product that, with fine-tuning, had great potential. That demo was of SalesWise. The company was early-stage, and I remember thinking this could be my next step. However, I had several consulting projects going, and couldn’t leave yet.
Fast forward to November, I ended many of my projects to focus on either building a company or building my personal brand. Well, I chose the latter by writing my book Postmortem of a Failed Startup: Lessons for Success (published Jan 2016!). Meanwhile, come the new year, I wanted to dig my heels into a product-oriented early stage startup. Then, one fateful day in December, I happened to see the CEO of SalesWise, Gregg Freishtat, at a coffee shop – figures I would meet him at a coffee shop. Don’t think he remembered me from October. However, we chatted for a split second, and made plans to meet.
We sat down a week or so later, and I learned the company was entirely engineers and himself. He had no other business-oriented employees. They’ve been focused on building the product and were at a point to go big – this got me excited. This was my opportunity to start from the bottom to help a startup grow while working with a highly successful entrepreneur and brilliant CTO in Jason Parekh.
I remember Gregg telling me he was looking for three roles – someone in marketing operations, an inside sales rep, and someone who knew conversion analytics. I haven’t had explicit professional experience in marketing operations or inside sales, but I have done them in my own startups in the past. I didn’t have the depth, but I knew that I could do anything given my ability to learn, adapt, and execute.
I admitted to Gregg that I didn’t have deep expertise in any one area, but I also wouldn’t “pigeon hole” myself to any one of the three, either. In my view, I would best serve the company at this stage and beyond by being great at all three – “start in sales to understand the voice of the customers – their needs, wants, objections, and value points. Then, I could approach at the macro-level with the marketing operations. From there, I would analyze results and drive conversion… the functions would flow”.
I started contracting with the company for January helping get all several marketing initiatives off the ground as part of the launch of the new platform, SalesWise 2.0. A couple weeks ago, I was offered a full-time position to which I VERY happily accepted. 

Okay, let me tell you about SalesWise…

This might sound like a product pitch because it is. But it’s a pitch to help illustrate why I’m excited.

SalesWise is a Sales Intelligence Platform providing comprehensive deal and relationship visibility and data sharing to sales teams to close more deals. SalesWise integrates a sales team’s most critical tools including email, calendar, tasks, documents, and CRM to automatically bring context and deal data together with no manual data entry. The platform enables sales leaders the full end-to-end view of every deal, every relationship, and every prospect to lead their professionals without constant catch ups and long sales meetings. Freedom to sell. Freedom to win.

Too wordy, here’s a slick video and some pictures:

This is the Sales Console – all your prospects in a single view that’s organized and easily filterable for meetings coming up, prospects with no follow-ups, etc.
This is the Prospect Card – it pulls your CRM data, email, contacts, documents, calendar… everything about a relationship. Best of all, I didn’t enter anything! It’s all automatically pulled in! You can also share this living, breathing card with anyone so they see what you see (read: collaborate!).

Why I was COMPELLED to accept…

  • After years consulting with other companies, I want to dig my heels into a product at an early-stage company. After all, I want build another product company in the future.
  • The founder is an accomplished entrepreneur having started four prior companies and having successful exits. I’ve learned so much from him already over the last month, and can’t wait to continue developing under him.
  • The engineering team is full of studs. Jason leads the charge as the CTO (hails from Georgia Tech) and every dev he’s recruited has great experience (ex-Google, instrumentation specialties, etc.).
  • The technology, as I said before, has massive potential for sales leaders and sales professionals. When I first entered the product, I got that “wow” factor. Having released a more focused product, responses have been extremely positive.
  • The company needs someone to lead marketing and sales. Count. Me. In. I want to be a builder of the company, and this will be a great place for me to flex my muscles and challenge myself as a leader.
  • Though the CEO has been very successful, he’s open to iterating and learning. I’ve met so many entrepreneurs over the years who use their prior successes as hard-set templates into new ventures even though businesses are completely different. Gregg understands the need to launch, learn, and iterate. He’s building for the long-term gains.
  • I realized over the years that I really enjoyed working alone partly because I stopped trusting others. I don’t want to feel like that. I want to be on a team where I can trust others, and others can trust me.
  • Gregg’s style of leading is conducive to my style of learning and executing. He reminds me of my previous Superboss, Irv Grossman. Both are very passionate (“intense”), intelligent, and great mentors. Gregg expects $hit to get done and thrusts a lot of trust upon me. I get a lot of responsibility, but he’s not shy to roll up his sleeves and do tactical work, too.

The gist…

It’s just a really great opportunity for me. The company is at a point primed for growth with a more focused product after having thousands of users on v1.0. The technology behind the product is exemplary with massive potential. The leadership team are complementary and the team as a whole are hardworking, bright talents. Heck, I’ve already met the Board, and they’re bought into the vision.
The last several years of building my brand, my network, honing my skills has led me here – my new chapter. My initial reason for consulting to find my Next Great Move actually worked. However, it was when I made a conscious decision (after several years of consulting) that I wanted to join a startup that I met Gregg. Just a couple weeks later, I jumped on board.
Time to do great things!
(By the way, if you’re in sales, you should check us out.)