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?

HR, Operations, Startup Sales, Startups

The one thing about meritocracy

Is that it can be not all it’s cracked up to be. At scale it’s difficult.

It’s much easier to point to someone’s tenure and title and say she or he is in line for the next promotion. They’ve “earned” it and really put in the time.

While this may or may not be the case, many idealistic startups prefer meritocracy.

The idea of a “level playing field,” free of bias, where individuals are rewarded based on capability is attractive to everyone.

Who doesn’t want meritocracy?

I believe it’s natural for larger organizations to fall into this pattern.

It is far more difficult to follow the tenure playbook than it is to run rigorous HR reviews, 360-degree feedback, keeping HR software updated, etc.

But also, it’s even far more difficult to do the above while trying to find the elusive product-market fit; to close deals when you’re still not 100% sure what you’re doing is correct as a startup organization in the first place.

Who has time for that?

So generally what I believe happens is that that initial intention eventually is replaced by the usual bureaucracy and politics. Biases and human flaws are magnified at scale.

And so far, there doesn’t seem to be many well-known, proven cases of a meritocratic organization succeeding.

So what are organizations supposed to do then?

The closest things we seem to have towards this utopia of an organization, is where extraordinary entrepreneurs and founders have iterated and built up scalable, more objective systems. And even then, they acknowledge the bias and inject into their culture

Ray Dalio’s Bridgewater Associates is the closest case in which he talks in depth about how he built up the BA culture over time; created HR systems for assessing and analyzing personality; built software to enhance accountability; documentation and content to track results and individual track records; and dives further into using concepts such as “believability” and honest feedback to achieve something.

(Suggestion: Read Principles as soon as you can.)

So why does this matter at an early stage?

If you’re a founder, it’s your responsibility to consider, build, and combat the challenges that the organization is going to face down the line.

In the startup world, everything is about scalability.

If those systems/frameworks are not in place or being built iteratively from the beginning, then it becomes exponentially more difficult to institute them successfully later on when you need every ounce of juice to hit your next KPI towards exit.

And as an individual contributor?

When your prospective CEO tells you that the organization is based on meritocracy, exercise caution.

Specifically ask how she or he plans on maintaining that meritocracy at scale and who is going to be responsible for instituting those as the startup evolves.

Ask how is someone going to objectively track meritocracy to ensure that it remains a founding principle of the startup.

Consider the down-the-line consequences – what happens if we’re acquired? How can you ensure that we’re going to remain a meritocracy?

Ask for title bumps. And often.

In early stage organizations, it might go “against” meritocratic values to have a big title. But the value of those titles do exist outside of your startup silo – they exist in public markets all over the world.

If a public company is going to acquire the startup you’re joining, consider how they will view your title.

Will the title port over for all the hard work you put into the startup system that lead to the acquisition?

Or is it a better idea to assume that your efforts may not be fully recognized? And that the higher your title at the time of acquisition, the higher your title at the acquiring corporation? Or that all of the associated perks and benefits are actually tied to that title being assigned to you by the acquiring corporation?

I’d argue the latter. Always assume the worst.

And assume that that meritocracy, being touted as a meritocracy, is likely not one and allow them to prove it to you.

Product-Market Fit, Relationships, Startup Sales

The Best Sales Pros

I’ve got a sneaking suspicion that the best sales pros and thought leaders out there come from girls and guys who have faced, and overcame, adversity in their lifetime. I really can’t back that up beyond anecdotal evidence, but to me, there’s a not-so-fine line between those that sell and those that are trained to sell.

That’s not necessarily to insinuate that the worth of these individuals is not the same or one may always generate more sales than the other,  but I do think it’s worth knowing or seeking to identify, who the best performers are going to be.  There will probably be an eternal “causation-correlation” debate on the matter. But when it comes down to it, and you can hire all A-players for your team, you’re going to aim for all A-players on your side.

There are those who follow the playbook, go through the motions, hit all their targets, get along well with their team, follow the pitch framework, and get promoted every few years. Until they then jump into the manager playbook and begin the process all over again. We’ll call these the trained sales pros (TSPs) who generally opt for companies already on their rocket trajectory.

And then there are those who sell who we’ll call the natural sales pro (NSP). These pros tend to attract people and naturally build relationships. They’re not comfortable being just a sales professional, but a genuine advocate and friend. Even if the prospect does not end up buying the solution, you will find seller and buyer connecting on LinkedIn, MSP, SalesStack, and interacting with one another. NSP’s are avid social sellers, have their own blog and personal brand, interact with, and support one another as sales pros.

I think these are the individuals a hiring manager should be aiming for to build out there outbound sales team. NSP’s have a story behind them, often of struggle and constant challenges. They didn’t have the silver spoon at birth and instead through their past journey and struggle found that this was the profession that fit them.

And these NSP’s are always impatient, outspoken, yet eager to learn, and can help take a raw product to PMF – often forming the same playbooks that TSP’s end up learning from.


Marketing, Product-Market Fit, Sales Process, Startup Sales

The Easy Guide to Product-Market Fit (PMF)

90% of startups fail because they never reach Product-Market Fit (PMF). PMF is a function of a variety of daily, outward-facing activities that occur at an early stage: customer & product development. This represents the basic framework all startups need to find success and to really begin scaling.

I have met, mentored, and seen too many startups and entrepreneurs waste valuable time, effort, and money chasing a problem that doesn’t exist, with a solution that no one wants. Enthusiasm and passion alone don’t cut it. Often, startup failure directly correlated with the lack of these critical development efforts. But you don’t need to take my word for it.

Steve Blank, esteemed Silicon Valley pioneer and author, is a huge champion of the process. His books and research powered a lot of Eric Ries’ thinking in the Lean Startup approach today which is generally the gold standard by which modern tech companies are run. And be sure to check out Marc Andreesen’s famous post on the matter here too.


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Customer Development is a formalized process in which the Entrepreneur and his team must “get out of the building” and ultimately communicate with their prospective customer base to identify the key ingredients to a successful startup. It’s a combination of all the “outward-facing” activities (e.g. sales, business development, followed by marketing) that the founding team must engage ideally before they go all-in with the startup.

Steve breaks it down into four steps:

  1. Customer Discovery – Who’s the customer base? What’s the problem that I’m solving? Talk to 50 potential customers and get to know them. Do this before you invest too much, if any resources, in building the actual product. Revenue should always be aligned behind. There’s enough data to begin developing a Minimally Viable Product (MVP) and core features that begin to help the Client overcome the problem you’re solving for.
  2. Customer Validation – Is the market reacting positively and buying your solution? Is there some semblance of process and marketing messages that are resonating positively with the customer base?  This is the beginning of demand-generation and the production of a marketing message that will further drive demand. The Product is there and new features are being added to the product that will continue to meet the clients’ expectations. The first sales are complete and the organization begins to understand what actions are required to move a buyer down the sales funnel.
  3. Customer Creation – Can the organization drive repeatable, end-user demand that gets added to the sales funnel? This is where the marketing message matures as more knowledge is acquired about how the clients’ organizations are run. The sales team identifies what the Ideal Customer Profiles (ICP) is, the key decision makers are, buyers, budgets, and processes and how to incorporate those key factors the decision. There are more data points, more customers buying, and more customers lining up to buy. There should be some level of inbound activity and the startup needs to understand and provide material to the customer along their Customer’s Journey. This is where the funnel starts becoming optimized, and the sales and marketing organization is able to provide the customer with resources that answer their relevant questions.
  4. Company Building – How is the startup going to scale? What departments and leaders need to be hired now to continue growing the organization and repeating the customer development process in a way that will generate successful returns? Are we maintaining relevancy as the market is changing? Is our product still #1?This is once product-market fit is obtained and the organization has crafted a product that is directly solving the clients’ challenges. Recruitment, hiring, HR, diversity, and other internal initiatives become more important.

Each of the above steps needs to be studied, understood, and executed. In theory, if this is done correctly, the entrepreneur confirms and defines the purpose of their organization and can grow into a larger enterprise. It is an iterative process that continues to propel the organization forward.

To close, the common theme you will find here is sales. This team represents the outward facing component of the business gathering new information to bring back to marketing, product, and other organizational leaders. They are key and critical to the company’s success and just as important as the idea itself. An early stage sales hire that understands this is key to the success of that organization – often more so than the founders themselves who are not engaging in sales related activities.

A team can have the best product ever, but without the right customer-interfacing mechanisms for adoption and growth, there is nothing.

In my next post, we’ll take an even deeper dive into the importance of an excellent early stage hire, the rescaling your early stage, startup sales organization.

Sales Process

Controlling the Sales Conversation


One of the biggest rules of thumb in sales is to control or own the sales conversation. That’s not to say bully, assume, be pushy, or put words in your prospects mouth or anything of that nature. Instead, the modern salesperson is arming their prospect with information (ex. content, stats, data, observations from other clients, etc.) when they need it.

In maritime law, when navigating closer to shore, there are regulations and rules for safe navigation. Keeping your vessel within the navigational beacons is one of those rules. If you stay the course,  you’ll make it to your destination barring any Acts of God. I like to think selling is the same way. A decent salesperson who follow the sales process, remains persistent, and has a viable product that solves business problems, will close if that customer wants to buy.

In modern sales, there’s rarely any traditional selling to do anymore. The “A-B-C” (NSFW) days are over. In fact, according to the CEB when it comes to b2b sales, 57% of the sales process is already complete if the prospect reaches out to you. All the information they need is at the fingertips, and they’re free to demo with any one of your competitors, choose a different solution, build their own – whatever they want to do.

It’s up to you as a sales person, with the best product, to intimately understand the prospects’ business (being an expert takes 10,000 hours), reframe and challenge the way they do business, unlock insights, and then present to them your product. Sales is a two way street for a reason – there’s intent to buy from the prospect, and it’s up to you to guide them through your sales process along the buyer’s journey.

An excellent way to do this is to plan out how you’re going to win accounts (following a sales process) and gain commitments throughout the deal’s lifecycle from the very beginning. Remember, your time is also valuable, and you will be solving a problem or generating significant revenue/results with your product.

There are two methods I recommend to approach this ‘control in sales:

1 – IF X, THEN Y

Scenario: After an introductory call, the sales rep needs to set the first demo and get that decision maker to attend the web conference.

Salesperson A: “So let’s set a demo for next Taco Tuesday at 5:00 PM.”

Prospect: “Great; I’m in. Looking forward to learning more.”

(Remember, it takes at least 5.4 decision makers to sign off on a sale. No one wants to personally absorb all the risk of working with a new vendor when they can spread this risk amongst colleagues.)

Salesperson A: Awesome. Do you think we can get the VP to join us on the call?  And maybe the Head of Success? That way we don’t have to hound them down later on and maximize our feedback.

Prospect: Yeah, sounds great. I’ll coordinate with her and confirm.

In this case, if the buyer can get her VP to join the call, then the rep will save the buyer time.  In return for the Rep’s valuable time on the demo, the ideal prospect will respect the rationale and work to get the decision makers on.

As you mature in sales, master rapport building, and get more comfortable engaging and speaking with the prospect, these conversations can be even more explicit. These sort of scenarios are more prevalent in complex deals (i.e. enterprise deals) where the prospect also has an internally complex buying process that you as a Rep will not know.

You can ask for something directly “in return.” There’s no hard and fast advice for knowing when to drop this one in your sales conversation. Use it when you feel like you’ve really nailed down a champion who speaks openly and freely with you and is exhibiting a level of trust in you. Or they need to get this done as soon as possible. Often this is going to be an individual who has clearly expressed their interest in buying your solution and is explaining to you what it’s going to take to get it to move forward.

2 – IF X,  GIVE ME Y

Scenario: After a qualifying call, the VP of Sales learns that an influencing buyer needs to get this deal done as soon as possible (one can wish right?) and that based on his research, the one key feature he needs exists only with the pro’s product.  It’s clear that the buyer is a champion.

VP of Sales: “Appreciate your time today. Before we jump to the next step, I’d like to ask one last thing of you. If I set some time aside to do research, prepare an awesome presentation for your team next week, and nail this deal with you, will you provide me a list of every decision maker in the room and what I need to know about them? I’ll send you a deal map I’ve been working on that I can use your help on filling in the blanks.”

Prospect: “Yeah, definitely. Send it over and I’ll fill it out right away.”

In this case, the seller is explicit with his or her ask. Fill this deal map out, and I’ll put together an even more amazing presentation.  The buyer gets what they want, and the seller obtains information that is critical to closing the deal. It’s another mutually beneficial arrangement.

Deals don’t close themselves. The onus on ensuring that the buyer’s needs are being met while pulling the prospect down their organization’s sales funnel rests on the salesperson.


Sales Process

Fun with B2B Funnels

At a high level, startup strategy is generally the same when securing revenue. There are tons of variations of the startup sales funnel, but generally, they can be classified underneath four activities that help acquire modern customers and build the business:

  1. Awareness – Marketing team produces the message, crafts, and pushes the content. The sales team is developing business through their own channels.
  2. Interest – Prospective client consumes Marketing content, and/or responds to Sales call request. The bulk of the education tends to happen here.
  3. Decision – Prospective client is educated, challenged by the company (read: Challenger Sale), and addresses any questions and concerns. This is typically where the sales professional has an opportunity to not only sell her solution but reframe the decision maker’s thinking – while making her product and organization look great in comparison to the competition.
  4. Action – The Client consults with their team and makes a final decision by way of a verbal commitment or signature on the dotted line.

Value is heavier towards the bottom of the funnel. Both parties mutually increase their engagement, devote more of their time, and transfer valuable information to one another. This value can exhibit itself in a variety of ways: from the rep educating the business owner, sending out company swag, to mapping out deal plans via sales methodology (ex. MEDDICC) These can be observations that the selling organization has seen or trends.

Usually, new pieces of insight and information the business owner is unaware of. In return, the prospect confesses their problems, struggles, and helps the rep map out how the deal is going to get done. This is where the sales rep has earned the opportunity to showcase his or her knowledge and expertise – and win the trust of the prospect.

Now you have startups flipping the funnel and engaging in more modern processes such as Account Based Marketing/Sales which specifically targets your ideal buyers. The framework above is representative of more traditional b2b SaaS which is the world I live in.  The beauty of startups, and why I choose this career path, is that startups are typically freed of “traditional” business practices and methods.

The beauty of startups, and why I choose this career path, is that startups are usually released of “traditional” business practices and methods. Entrepreneurs can play around with the different types of sales processes and methodologies within the funnel that work best for their product, industry, customers, and organization.


Powering up with your Peers

Put down the ROI for a second. Yes, you’re right – we do need more revenue, growth, and we do need to maximize our revenue-building time. But we are social creatures and functions of our environment. The environment, tech ecosystem, surroundings, whatever you want to call it, helps shape who we are, what our companies do, how our strategies are formed, how to obtain growth, and also help us to think in new ways.

Real relationships come in all shapes, forms, and sizes. You have:

  • Family
  • College friends
  • Team Members
  • Industry peers
  • Field peers
  • Advisors, Mentors
  • Board Members
  • Prospects
  • Clients
  • Mentees

Each unique relationship that falls underneath these silos provide unique perspectives, advice, guidance, and outlooks. They also can help when you’re in need. Paying it forward is great, but relationships need to be actively managed. Relationships shouldn’t be strictly transactional, but I do feel that relationships are made up of a series of transactions, over time.

They build:

  1. Familiarity if you meet someone for the first time. Perhaps you’re sharing a few extra details on the presentation you made. They know you as that person who knows x or y.
  2. Credibility as you engage and share what’s happening at your organization or challenges in life. Usually, this is is a result of repeat interaction.
  3. Trust. This is the “closed deal,” the outcome you’re seeking. These relationships represent the ultimate outcome in which you can bet on someone and their word because you know them so well. You no longer question them and their expertise. Instead, you lean on them, or they lean on you for their professional or personal advice.

We’re never perfect as human beings, and we should always strive to be intellectually curious. Sales professionals especially should always be in a constant state of learning and networking. Regularly take time out of your week to meet with these people. It is a continuous cycle of actions representing giving and receiving.

Close the deals, but maintain the relationships so you may continue to grow as a person.


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.

walt disney forward.png




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.

hunter walk

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.