Cargologik, Marketing, Product-Market Fit, Relationships, Startup Sales, Uncategorized

The Joys of Early Stage Sales & The “Soft Guidance” Ask Gone Awry (CS#1!)

Decide to do a demo for a good friend of mine who belongs to a global leadership group. Members share their needs across the group.

My buddy, a member, upstanding entrepreneur, and fellow logistics stakeholder & entrepreneur here in Miami. We collaborate w our peers on city-wide initiatives w the Beacon Council.

We level set expectations….”not exactly what we do, but some of that functionality you’re looking for.” Nonetheless, the entire exec team hops on.

Sons of the owner/IT hop on first. Super personable, friendly, considerate.

Pops takes a few minutes to join, and when he does the conversation starts great. He starts sharing his problems and his needs.

I explain to him what we do, and explicitly mention PO management software – knowing that this likely wasn’t a deal in the first place (wanted to learn).

Father, who sees the demo for a whole one min, talks about how they don’t need new software and that they can just “trust” the broker/forwarder to hold up their end of the bargain. And meantime complaining also about how in 30 years he’s experiencing his first major transit delays trans-pacific.

He leaves 25 min into the call. I always appreciate being mindful of each other’s time, just like anyone else.

I DO NOT appreciate someone telling me that this is a useless demo and leaves abruptly, zero regards for his team who stay on and politely say bye to me.

It doesn’t matter how much experience you have, with regard to whatever industry, we can all benefit from having productive conversations. Even if “not a fit,” individuals should always be striving to have conversations that help stretch their thinking, perspectives, assumptions.

Especially companies that have been around for “30+ years.” In the same way, we seek to maximize conversations and ideas with larger, more enterprise players that we also know we have nothing to sell to.

It provides a trajectory, almost a “soft guidance input,” as you seek to define and flesh out your strategy over time. Especially the go-to-market, where things are fluid, and shift all the time.

Have you guys had any issues similar to the above where you encountered someone with the wrong mentality in a sales conversation? How do you navigate the scenario? Have you ever been able to salvage these types of interactions/relationships? Or do you just pass on them?


Moving On & Looking Back

It’s over. Two and a half years of blood, sweat, and tears has finally come to an end.  In my heart, I knew it was coming, and it finally came.  And after a brief 20-minute conversation with my CEO and friend, I was told the team was let go, and we were shutting down our “cash cow” product.  This moment also signified the start of the next chapter in my career and development. But this one is going to leave a mark because it was my first startup where I made my best friends, built a vast network, and sold into some of the best organizations.

It was an emotional and honest conversation with one of my best friends and former CEO in which we both decided it was time to part ways.  I felt that I had given everything I could have possibly given to the company, and there was nothing left for me to do.  My Sales Team & I tried so hard to fix outbound sales and put together some semblance of “Predictable Revenue” but to no avail.

It didn’t matter anymore because no matter how hard I hired, trained, demonstrated, pitched, presented, negotiated, sold, and business developed; the needle just wasn’t moving anymore.  We were missing quota consistently; new sales tools and methodologies weren’t helping anymore; more conferences weren’t accelerating business development; a new VP of Sales and Board mandate for revenue now failed to change anything.  Outbound sales was a failed exercise over the past two and a half years, and it was time to change strategy.  One in which a sales team was no longer required.

But I believe everything happens for a reason, and as I discussed the scenario with my friends and mentors, it became apparent that this was the right move.  As I spent the next few weeks dwelling upon what had happened, why we ended up where we were at the company, and what can I do better in the future at my next startup, it all became very clear.  I knew what the right “ingredients” were to look for in my next organization, CEO, product, market, funding, comp structure, etc.

Startups are like family, and the industry becomes your world.  Everyone has to wear multiple hats and support one another and as a result, you end up growing very close and experimenting.  You learn a lot about everything; how everyone prefers to communicate; how they tend to think; what they’re passionate about; what their strong suits and weaknesses are within their roles, etc. It becomes your world. Your business becomes your environment and what you talk about at happy hour; your competition shows up in your dreams, and market and expertise thrill you and command mindshare.

But this startup world that we live in is, unfortunately, very limited in perspective.  You’re the fish underneath the water surface that doesn’t know it’s in water. It’s part of being human. But I found that the more I spoke about it and shared my thoughts, they were validated and augmented by my friends and family.  It’s the pre-mature NDA when you should be sharing your idea rather than protecting it.

By opening up, it allows you to become more personally and professionally aware and to carry with you the lessons to improve your value and the organization in which you join next.  Don’t be afraid to share with others. Let them challenge your assumptions and motives – you’ll still be learning either way.

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Life is all about learning. We get better each and every day through experiences, process them, create best practices, and then hopefully apply and execute them in our day to day life.

I choose to work in tech because it’s a lifestyle. It’s not “work” and “play” to me because it’s all the same. I enjoy my job in the office as well as at home, on weekends, and vacations.  How “work” manifests itself may be different, but at the end of the day, it all comes down to experiences.

In my world, the world of Modern SaaS sales, I create experiences that help build my expertise and allow me to become better than I was the day before.  This self-improvement can be anything from going to a business development event after work, taking a coffee meeting on the weekend, helping other fellow entrepreneurs and salespeople, and also absorbing knowledge from my peers and predecessors.

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The mediums I prefer to assimilate SaaS knowledge is typically in the form of books, blog posts, university reviews, studies, videos, and podcasts. I was dwelling upon this the other day and thought that if all of this information is out there, then why do 90% of startups still fail?  (Actually, the best explanation I can find in the first few results of Google is here. Thanks, Neil!)

I like to think about this questions as the beloved open-book exam. Some of the pupils will know better and prepare a “cheat-sheet” while others will wing it.  In the startup world, we’re typically taught just to wing it (pun intended), jump off the cliff, and build wings on the way down. But if you could learn to pick up on the signs, the indicators that there’s a cliff up ahead, and do research on how to quickly build those wings mid-flight, the chances are that you would.

And herein lies the challenge of the startup world.  You hear it so many times from VC’s, Angel Investors, accomplished entrepreneurs, CEOs, etc. that it’s about the individual entrepreneur and the team. It finally clicked for me, two years into my adventure at LiveNinja.

Success isn’t about who has the greatest product. Execution determines your success – and execution is a function of your team.


When One App Rules Them All: The Case of WeChat and Mobile in China

In case you haven’t been keeping up, messaging is the future and why all apps “expand until they incorporate messaging”. We all love and use text messaging…but there’s so much more that can and should be done here in the US. I’m surprised that weChat isn’t making a bigger push stateside. Time will tell who will capture this market, but it’s going to happen sooner or later, that’s for sure.


How to Beat Bonobos & Warby Parker

Andy Dunn & Bonobos just launched their 13th Guideshop in Atlanta.  The notorious menswear e-commerce company, launched in 2007 by housemates, Andy Dunn & Brian Spaly, while attending Stanford Business School.  What started as a just company producing better pants, evolved into a full fledged menswear line including suits, jackets, blazers, By 2013 they had raised over subsequent rounds $130 MILLION dollars. 2 roommates & an idea. And 6 years later? $130 Million dollars invested.

Warby Parker, another e-commerce company specializing in glasses, has also joined the ranks of companies embracing the omni-channel customer experience. So why does a thriving e-commerce company open up 8 stores, and 4 showrooms?  Because there’s a large untapped market who will not simply buy their glasses online, and/or who might want the convenience of being able to try on glasses in person and/or the instant gratification of purchasing a new stylish pair of glasses.  Of course, they already had a established themselves in the marketplace so it wasn’t like starting a new venture from scratch.

There’s a new trend these days and NEWS FLASH: It’s all about the customer.  Customers are no longer buying into your product – they’re buying into the company as a whole.  New generations want personalized service, whenever and wherever they want it.  Additionally, they’re buying into the brand, customer support, social media presence, innovation, and ultimately the customer experience.

Organizations and processes can get complex at time but if you stay focused on the customer, like these brands have, you will find success.  A recent study put out by Watermark Consulting conducted a study to try to better define the ROI that’s associated with customer experience efforts.  The study found that the customer experience leaders that “market Leaders outperformed the broader market, generating a total return that was 26 points higher than the S&P 500 Index.”

How are some ways that your brand or organization are innovating around customer experience?