Traits of Top Salespeople

"Top salespeople are versatile: they can change their approach based on the person they are dealing with."

Author: Sean O'Shaughnessey
Are You Able to Make Small Talk?

Are You Able to Make Small Talk?

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Casual conversation or “small talk” helps you sell yourself, which is frequently the most essential thing that you have to sell.

If you have read my book Eliminate Your Competition or you have read much of the pages of my blog, you know that I frequently talk about the importance of selling three different things:

  • Your product
  • Your company
  • Yourself

In most industries, your product is probably very comparable to several other products on the market. It may be slightly better in a few areas, but it is likely marginally worse in a few different areas. Essentially, it is usually a tie on the features and benefits of the product. The brutal reality is that if it is not a tie today, then it will likely be a tie in the future.

I am sure your employer is fantastic. I also assume that the company that wants to beat you is excellent. While there are undoubtedly differences, there aren’t that many companies that are so awesome that it is the primary reason that you make a sale. In general, companies in the same market are mostly a tie.

That leaves you. In most cases, you and your virtual sales team are the primary reason that you win or that you lose. You have undoubtedly heard the old adage that you didn’t lose; you were outsold. Few deals are truly won or lost on product and company – it is typically the sales team that makes the difference.

The sales team understands how to apply the product benefits to the individual needs of the people making the decision. The sales team knows the correct people that will be interested in those small variations of company benefits.

In order for the sales team to have this capability, every decision-maker in the organization must trust you, and hopefully, they respect you. The best ways to do this is through your innate knowledge of:

  • their individual goals
  • their collective goals
  • your ability to relate the correct information to them in keeping with their goals
  • your ability to engender trust in other people

You can develop confidence in other people by your ability to speak about you, your company, and your product. However, you can accelerate that trust if the decision-maker personally likes you. Personal likeability is not a pure requirement, but few people will trust someone if they absolutely do not like the person. In other words, you do not need to be a personal friend to the various decision-makers, but you definitely cannot be a personal enemy.

Personal likeability is the primary reason that you need to be good at small talk. It makes you a human. It elevates you beyond being the smartest person in the room; it means that the most intelligent person is also a friendly and enjoyable smart person.

If you have read my book Eliminate Your Competition, you likely know that I think that acronyms are quite helpful. I recently came across this tweet on Twitter that creates an acronym for the primary aspects of small talk.

FIRE is a great reminder, and I suggest that you have an “ice breaker” story or two in each of the four categories.

  • Family
  • Interests
  • Recreation
  • Entertainment

During small talk, you’ll get some idea of that odd-shaped part of a human being that’s invisible to the eye and impossible to articulate. Are they kind, hurting, silly, or malicious? Some combination of all of those?

Mastering small talk will help you find common ground to create a mini-bond with new contacts. Small talk may feel trite and unimportant, but it’s the small talk that leads to the big talk.

Ideally, small talk will uncover common interests, business alignments, the six degrees that separate you, the potential need for your product, and basically whether or not you enjoy each other’s company. The goal is not to become best friends or a new client on the spot.

The goal of small talk is to establish enough common ground to determine a reason to connect again.

Keeping a conversation rolling is simple when you learn to listen and ask appropriate probing questions that naturally grow from the dialogue. You only need to prepare a couple of questions in advance. If there is a genuine connection, then you can proactively engage in conversation.

There is a balance between too much and too little business talk. If you don’t talk business at all, you may miss an opportunity to communicate who you are, what you do, and what you have to offer and that you are competent in your field. There are some people who you can know for years and never hear them talk about work. You assume they are retired or not interested in more clients.

Match the depth of dialogue to the environment

You don’t want to let people overhear confidential or inappropriate information. Plus, talk that is too deep at business functions can lead to heated conversations. Over-heated conversations can quickly be subdued by merely making a statement that offers little room for a rhetorical comment. This tactic will diffuse the situation quickly and without incident.

For example, say with a smile, “Well, that’s one issue we’re not going to solve over lunch,” or close the conversation with “I understand your perspective,” minus the “but” that would aggravate the situation.

You won’t win points for always having to be right. You may win the debate while making someone else look bad, but in the end, you’ll make yourself look worse. You will, however, earn points for having social graces if you are the bigger person and cool potentially fiery situations.

You have to know when to let go and kill the discussion even if you believe you are correct on the issue. In the grand scheme of things, we must value the opinions of others and accept that it is not essential to win every debate. The last thing you want to do is to appear as the know-it-all who must end conversations as the perceived winner.

How you make people feel will be remembered

When it comes to small talk, don’t think you must say something amazingly insightful each time you speak. People will likely forget your words but will remember how you made them feel.

No doubt, small talk can get a little dull after a while. So, take it upon yourself to make it enjoyable. To prepare for conversations, rely on FIRE (described above). These will make it easy for you to swing an otherwise stale conversation into one that makes you a genuinely enthusiastic conversationalist.

Have you ever been in a conversation that wasn’t clicking, then suddenly the mood changes, and you both have a smile on your face as the conversation starts firing on all cylinders? That’s because you found common ground. It occurs when two people have an interest in the same topic.

By determining in advance what interests you, half of the equation for stimulating conversation is complete. Now your job is to guide the conversation from topic to topic. Your goal is to solve the foremost half of the equation: What’s of interest to your new contact?

You need to be good at this!

The real key to great conversations is to relax. Let the conversation flow naturally. That’s easiest to do when you’re fully engaged and genuinely interested in the conversation topic and the person with whom you are talking.

When you make small talk, you are primarily selling the one thing that you are the premier expert on: you. Since you are typically the reason that you will eliminate your competition and win the deal, you should practice it until you are extremely good at it.

Header photo Conversation by Sharon Mollerus on 2006-05-17 10:08:20
Going From Enterprise Sales Manager To Startup VP of Sales? Velocity And Focus Are Your New Normal

Going From Enterprise Sales Manager To Startup VP of Sales? Velocity And Focus Are Your New Normal

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The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” where we discuss your promotion from individual contributor to leading a team. Is it for the faint of heart?

Navigating the move from enterprise executive to startup VP of Sales or Chief Revenue Officer is not for the faint of heart. However, for successful managers, the disruptive nature of startups can be cathartic.

You are probably a lot like me. You went from an individual contributor or a front-line sales manager for a big company with lots of resources to a team lead at a small company with limited resources. A sales manager at a major corporation and an executive at a startup may seem like they have more differences than similarities, but experience in the former helps inform the latter.

For executives considering doing this move (or if you have already made the jump), this move is wide open with opportunity. Here’s how to take advantage of it.

Know Your ‘Why’

The grass is not always greener. Startups are not a reprieve from corporate life; they live on the razor’s edge of “scale or die.” Time and mediocrity are enemies. Startups typically move fast to create solutions that can scale across industries and sectors.

In this environment, it’s important to have a “why.” The “why” is different for every executive — and truthfully, it can be quite personal. Some questions executives may want to ask themselves while considering the move include:

  • Do I want to build solutions to problems I’ve encountered throughout my career?
  • Do I want to get back to creating?

For example, our customers get the benefit of Kubernetes. According to Gartner, containers and using Kubernetes to orchestrate containers is the de facto choice for the next generation of software infrastructure. When I saw the reference architecture for Agile Stacks, I knew we had a game-changer that enterprise buyers need because every company on the digital transformation journey must build software better and faster. And the velocity, matched with a rigorous focus, is what I need at this stage of my career.

Find Your ‘Who’

I was introduced to my current startup by one of their Board members that I have known for years. When I met the CEO, I found that we shared similar industry observations, and I found myself excited about his market vision, company, and approach.

If you are joining an existing founder, you have a lot of research that you must do and it won’t be as easy as joining a big company with a lot of documentation. Research the company beyond financials, business model, product, and technology. Understand the startup’s culture; invest time and effort into exploring whether the executive-partner relationship can build a foundation for mutual success.

Assess Your Industry Expertise

Soon after talking to the company, I realized my new company had built actual solutions for some of the problems I had on the enterprise side. I could leverage my industry expertise to help the company execute its product vision, accelerate time to market and deliver quality solutions. When I considered leaving a global enterprise for a startup, it had to be the right one.

Startups should meet or beat milestones, and the industry expertise of their leaders can be a driving force to provide rigor. Executives must self-assess how deep and how broad their industry knowledge is. Do you fully understand the ecosystem and how you can help a startup impact, and potentially lead, that industry? Can you bring market vision, build strategic partnerships, drive maturation in existing products, expand the book of business, develop talent, deepen customer relationships, or create operational efficiencies to enable faster growth?

Fight Through Ambiguity

There is no room in a startup for executives who are unwilling or unable to be operational and visionary. It is not possible to understate the level of foresight, flexibility, and agility required in this environment.

You must continuously recalibrate your approach to operational efficiency, as working with limited resources forces me to ensure I am creating value at every turn.

Create Value

Within many large companies, the Silicon Valley mantra of “move fast and break things” doesn’t necessarily translate. Large companies have the resources, money and institutional support unavailable to start-ups, but they rarely have the focus to solve industry-sized problems. And they must measure and manage risk daily.

Further, while startups are relatively flat, large corporations are highly matrixed. In order to be a successful sales executive, it’s imperative to build relationships across departments. People need to trust that moving forward will benefit them.

Any executive joining a startup should focus on the value they create as an individual. What do you bring, above and beyond the job for which you were hired? Ask yourself if you have the emotional quotient (EQ), for example, to serve as a translator to the enterprise on how to evaluate product fit while coaching a startup team on how best to work within enterprise processes for implementation. That’s creating value for both sides.

Get Accustomed To The New Normal

Velocity and focus are my new normal. You must create more with less, fast and with laser-focus on impact. Startups can accomplish more in weeks than a large company could do in years, if at all. However, that rapid advancement can easily cause the company to go into disarray. It is simply not enough to have velocity, you need to have velocity towards your goals as a company.

This post originally appeared on my blog series on my company website “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup.”
Five Habits of the Best Salespeople (and how they differ from their underperforming peers)

Five Habits of the Best Salespeople (and how they differ from their underperforming peers)

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Are you doing things every day to make you a successful salesperson? Are you following the best practices of top salespeople?

For managers, do you know which traits to encourage in your reps? Do you have a plan to make them better by pushing them in the right direction for success?

1. The top salespeople spend more of their time selling. High performers spend 36% selling than their peers. Top salespeople spend 19-23 hours selling per week, but average salespeople only spend 14-18 hours selling per week. Spend time focusing on activities that generate revenue. 

If you want to be a top salesperson, you need to spend time focusing on activities that generate revenue. It is not uncommon that salespeople will complain about being dragged into non-revenue generating activity, but few maximize their time. This also means that you need to understand that being a top salesperson is not a 40 hour per week job. You need to delegate the time-draining activity to weekends and after hours. When are you doing your expense reports (hopefully on Saturday morning)? When are you sending thank you notes and follow up emails (hopefully in the evening while helping the kids with homework)?

2. Top performing salespeople don’t give up easily. Top performers will try to contact a lead nine or more times before giving up. Average performers will only try to reach a non-responsive lead five times before moving on.

This activity doesn’t have to all be once-per-day phone calls. As I explain in my book, Eliminate Your Competition, you should be developing your own newsletter for maintaining a relationship with your customers, your top leads, and your cold leads.

3. Top performers are driven individuals. When asked to discuss their traits, 81% of top salespeople rate “being driven” as being very important. Average reps only said this 57% of the time.

4. Top performing salespeople think critically. When surveyed, top performers rate “critical thinking” as being essential to their success while only 40% for their average performer brethren.

5. Surprisingly, high performers tend to be more independent. Top salespeople solve their own business problems and are not needy of their manager. Sales managers report that they spend 30 minutes less time per week than their average performers.

Part of the reason that sales managers spend less time with their top-performing reps is that every manager wants at least a moderate improvement in rep productivity. By definition, it can be easier to get more net growth from a low performing rep than a top-performing rep.

However, to be a top salesperson, you need to be able to run your business. You can count on your manager for “air support” in times of need, but you need to have your own plans for moving your prospects through the pipeline and making small customers into big customers.

Following is a video that gives a few more details to these five critical traits.

Header Photo by OpenClipart-Vectors (Pixabay)
As Mark Cuban says – the market size is almost immaterial

As Mark Cuban says – the market size is almost immaterial

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This post originally appeared on the blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stack website.

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” where we discuss ignoring market share and simply focus on selling and your customers.

Do you watch Shark Tank? If you are in sales at a startup, there is probably no other television show that is as relevant to your life as Shark Tank.

Shark Tank is the television equivalent of a VC conference. Entrepreneurs pitch their ideas to five extremely wealthy people and try to get them to invest. In a startup, if you are not personally responsible for talking to investors, your manager probably is doing it.

My company, Agile Stacks, where I am the Chief Revenue Officer, will never go on Shark Tank. Not because we don’t want the attention of these well-connected investors, but because we are already too well-funded and too large to consider them taking a substantial portion of our company which they prefer to control.

There is one consistent sign that the entrepreneur is going to be rejected by the Shark Tank panelists. It is when the founder starts to talk about how massive the market is for their product. Mark Cuban is usually the first to pounce on this aggressively, and often it is his reason for not funding the startup.

If you are brand new and haven’t sold a single product, then regardless of your targeted market, your market share is 0.00000000% (take that out to an infinite number of decimal places). As soon as you start to sell, the number of decimal places gets fewer, but through most of the time as a startup, you still have well under 1% of your market. You can have an incredibly successful startup and have a meager market share.

Almost every day, the companies Uber and Lyft are in the business pages. They are the big guys in the peer-to-peer ridesharing market. But they are incredibly small in the drive-to-some-destination market (which is dominated by people that get behind the wheel and drive to a destination). On most American streets and highways, not 1 vehicle in 100 on the road is a rideshare car (obviously this varies by city).

Until Uber convinced their first customer to get into a car with a stranger, the peer-to-peer ridesharing market was tiny. It didn’t matter though. What mattered was that the founders thought they could build a company by making it easy, convenient, and affordable to get paid for driving people around in something other than a taxi. They built a product that they thought people wanted, and then they went out and convinced people to try it.

Market share simply doesn’t matter. What matters is getting those first customer purchases and making that customer happy with your service and product. Then get the next purchase (and the next, and the next….). It is only customer purchases that matter and the satisfaction of your customers with your product. 2020 for Agile Stacks is all about traction, I’ve come aboard and inherited a sales team. We rarely discuss market size on my weekly pipeline calls. My drive is to focus the team on working the deal to close. That is what’s important to my leadership and my Board.

Nothing else matters. Just go sell something.

Header photo is courtesy ABC.
Selling without being sold

Selling without being sold

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There is an old saying that everyone sells. I believe in this saying. As I explain in my book, Eliminate Your Competition, selling is nothing more than helping someone make a decision that is favorable to you.

My life is business-to-business (B2B) sales. My book is designed for those sales situations and most of the advice on this site is geared toward that audience. However, I am frequently most impressed and most unimpressed with a particular type of business-to-consumer (B2C) salesperson: the waiter/waitress at a mid-high level restaurant.

Did s/he make a special drink for you? Accommodate you with a different type of water? Offer suggestions on pairings of wine with your plate? Suggest a particular dish based on feedback from other customers or even personal tastings or observations of the raw food that arrived earlier that day? Perhaps, encouraged you to try today’s chef special (which almost always has a slightly higher margin for the restaurant)? And of course, checked back 2 or 3 times to make sure that food was prepared to your liking and offering a further refreshment from the bar?

When we go to a restaurant, we expect the food to be exactly correct. There are too many choices in any mid-size or above metropolitan area if the food isn’t excellent. However, my favorite restaurants are where the servers are amazing.

I live in Cincinnati. My favorite restaurant in town (where my wife and I will celebrate her birthday in a few weeks) is where we ask in the reservation to be seated in David’s area. There dozens of fine restaurants in downtown Cincinnati but David’s restaurant is where we go on special occasions, and it is primarily because of David.

David has been our server for over 5 years. We know that his service and recommendations will be fantastic. My wife will likely order one of her two favorite dishes that the chef prepares to a standard that is probably unmatched in downtown Cincinnati, but I will experiment. David will guide the choices of my appetizer, entree, and dessert.

David is our Trusted Adviser at this restaurant, and he fulfills that role splendidly. He will recommend a couple of wines based on his knowledge of our tastes and our dishes and perhaps steer us to wine by the glass if our meals are not complimentary (driving up the profitability of the restaurant). This is the role of a salesperson. Better service, customization, and higher customer satisfaction at a higher profit. I know that I will spend more money with David than another server, but I also know that my wife’s birthday will be even more special.

Salespeople excel when the quality control of the product that we sell is fantastic. This means we don’t need to cover for an overdone or under-seasoned dish (or outside of the restaurant world – a product or service that was not made to par). We can focus on other high-value activities that add continued relationship value to our customers.

However, working at a business with excellent quality control is only part of the reason for the success of a salesperson. What did you do to offer extra value to your customers? Are you part of the success of that restaurant in the eyes of the customer?

In my book and on these pages, I frequently say that there are three items that each salesperson sells:

  • your product
  • your company
  • yourself

If any single one of these three things is missing, then you risk winning the deal. In the case of David and his restaurant owner, you risk that we will go to another fine Cincinnati restaurant on the next special occasion.

Header Photo waiter by zoetnet
Finding the right channel to the market

Finding the right channel to the market

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This post originally appeared on the blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stack website.

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”, where we discuss the ways to check yourself when designing your sales channels.

This post is primarily for my peers as sales leaders in startups in the software market. If you are like me, you probably have years of experience selling for great companies where you refined your sales skills. You were a front line and second line manager for several years. You may have also helped some startup companies that didn’t really ever start.

Now you are in a new young company, and you are trying to sell a product that has never been sold before. There are a lot of very talented people in the startup. Like the fable of Damocles’, there is always an unseen yet prevalent pressure. And what you do to hit your sales forecast is to fall back to old habits. For example, you probably designed your sales force around a similar structure from a prior company. If your background is big software sales like mine then, you brought on a couple of big hitters and enticed them with stock options (because you couldn’t promise them a pipeline). If you are used to channel sales, you may have recruited some sales partners to bring your product to the market.

Whatever you decide, you need to question it. Here are some ideas:

Direct Sales

  • What are all the pre-sales activities in my deal cycle? If you are in the enterprise software market like my startup, Agile Stacks, and have a platform on new technology like containers, Kubernetes and Infrastructure-as-Code, then consider part of your deal cycle will require education almost as long as closing the sale. Consider the time burden you need to carry to educate. Also, consider how market forces such as analysts or journalists can shortcut these pre-sales activities.
  • Can marketing create 3x in demand gen? This one is really all about the math. Having a good (not great) marketing team to find your customers are is critically important. Make sure that you are teaming with the CMO to ensure messaging is in sync, and a frictionless strategy is in place for campaigns. Every marketing person I have ever met dislikes being considered part of sales, however, they love being part of the revenue equation. Going with a direct sales model demands that marketing be part of the whole process regardless of departmental assignment.

Channel Sales

  • Am I selling lipstick or am I selling machine learning automation? Obviously, these are completely opposite product categories. Whether you are a consumer product or enterprise offering, partners and alliances can be useful if you feel that sales velocity can be better achieved by the reach of players already established in the market. Also, do a quick read of How to find the perfect partner as a SaaS startup from my Business Development peer here at Agile Stacks.
  • Does my product require a heavy service implementation to it? My very strong opinion is that tech startups should never compete in the systems integrator market (unless your startup is a system integrator). If investors see an imbalance in your revenue model (e.g. services is greater than licenses) then you are a less attractive investment. The solution is to let partners handle the implementation.

OEM Sales

  • Are they big enough to make an impact? Since we at Agile Stacks are in the new category for DevOps automation, there is still an uphill climb to be well recognized. Luckily, we have a great partnership with HPE because they are an investor. But not everyone get this off the bat. Make sure to do your due diligence in the OEM’s market size and growth trajectory.
  • How far out is the inflection for ROI? Incumbent tech companies will be very interested in what you are doing but don’t be fooled – the negotiation is a very long road. Ask yourself whether the time and effort is going to help sales this quarter or next year. Startups cannot afford to graze. Find OEMs that fill a gap. For example, I look for conversations with our brethren in the hardware space because they are great at making stuff that goes in racks. And I make great stuff that runs Kubernetes in those appliances.

Nothing guarantees a failed startup (or a startup that didn’t start) like no revenue. There are a lot of reasons for a startup to not start:

  • Developers are not as good as they thought, and the product just simply doesn’t work.
  • Marketing missed the market and didn’t know what prospects would spend money on.
  • The CEO and CFO couldn’t convince investors to give the company time to mature.

The worst one though is your fault as the VP of Sales or Chief Revenue Officer – you didn’t set up the right way to sell the product.

The good news for the company is that you can be fired and your replacement might have the trust of the investors to have enough time to fix your mistakes.

Or, maybe you should be flexible. Don’t set up the sales channel that you are familiar with, but instead develop the right sales channel to make your product fly off the proverbial shelves.

Let me close with a reference to Episode 24 of Reid Hoffman’s project called Masters of Scale. In this episode, he interviews Mark Pincus, Founder of Zynga. The resonant quote from the interview, “I believe you have to be relentless about pursuing a big opportunity — and ruthless about killing your own bad ideas along the way.” Flexibility and experimentation is key to success when you are selling a product that has never been sold. Don’t be stuck in your ways. Design a sales model that works for your product even if it is a different model than what you’ve done in prior companies.

Header photo “Indirection” by virusslayer 
Don’t let pricing be the jab that knocks you down

Don’t let pricing be the jab that knocks you down

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This post originally appeared on the blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stack website.

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”, where we discuss the challenge of finding the right price.

One of the challenges of a new company with a new product is pricing the product. Every software startup struggles with this. It is almost impossible to make the correct decision for all time.

Be Introspective

Warren Buffet says, “The single most important decision in evaluating a business is pricing power. If you’ve got the power to raise prices without losing business to a competitor, you’ve got a very good business. And if you have to have a prayer session before raising the price by 10 percent, then you’ve got a terrible business.”

In all my years at this, pricing is never an operation to be taken lightly. Defining pricing means asking yourself and your founders’ questions about your product’s value. In some cases, you may be asking questions about your company’s value. In all cases, let the conversation flow because you need it to happen before stepping in that metaphorical boxing ring. Pull your team together and ask:

  • Should the product be free (like many of the Google products or Facebook) and the goal of the company is to use that free product is to gain a relationship with its users to sell other products? 
  • Should the product be so expensive that the company only needs to sell a couple every year to make its sales goals?
  • Should the product be one upfront payment with maintenance payments that enable enhancements to the product?
  • Should the product be an annual (or monthly) subscription fee?
  • What is the price point that we should choose for the product? If it is a new product, it is likely that it doesn’t have all of the features and therefore benefits that it will have after many more releases.
  • Should we price the product at its ultimate value when all of the features are built? This means we will sell through the natural objection that the price is higher than its current value, but it will become more valuable over time.
  • Or, should we price the product at a lower value and then increase the price over time as the new features start to add more value? This, of course, forces difficult conversations for price increases.

There are no easy answers to all of these questions. But then again, is there a best way to take a right hook? Certainly, there are ways to deflect and lessen the blow. At the end of the day, you still got hit. After a prospect conversation on pricing, if you are still standing, think deeply about what you heard because that is golden feedback before the next bell rings.

” Prospects tell the truth with their wallet. “

You Will Take A Right Hook, for now

My best advice is flexibility. Market forces are constantly changing. Assume that your price and revenue model are as good as possible with the information you have at this time. As a young company, you probably haven’t taken a right hook jarring you to your core. That’s OK, and maybe you’ve been lucky – for now.

No answer on pricing or packaging needs to be permanent. No decision can be forever in a new software company. Many famous soldiers, including Dwight Eisenhower, have said essentially the same thing. Ike said, “Plans are worthless, but planning is everything.” More recently, Michael Tyson modernized this by saying that all plans fail once you get hit in the mouth.

Go out and get hit in the mouth a few times by prospects, then make a new plan. Such is the reality of your pricing. Your pricing schemes and revenue models do not mean anything until you sit in front of a prospect. Did the prospect say, “Yes” immediately? Then you may have left money on the table based on your current value and your future value. Did the prospect say, “Yes” until they heard the price? That could mean a reasonable benefit/cost relationship someday, but maybe you need a few more features to justify that price.

Focus On The Footwork

A fundamental in boxing is being light your feet with great footwork for agility. Standing like a log, I can guarantee you will be hit with hooks if not a rapid flurry of jabs. And over time, your competition will wear you down with better pricing models. Get on your toes, take a few hits but miss the knockout punch.

If you don’t have bruises on your face, convince your leadership team to increase your price. If you are bruised and battered like you went ten rounds with Mike Tyson and have no sales, it may be time to lower your price, or really lean on your product team to add more value to the product. We all know that “No!” actually means “Not yet!” The challenge is how many rejections do you receive and how hard is it to get to “Yes!”

Your subsequent moves are essential. Did you raise the price for the next prospect after too many quick deals? Did you discount the list price to address a prospect’s hesitancy? Did you permanently cut the price by lowering your list price in the hopes that future features will allow you to increase the price? You have to document and learn from every interaction; otherwise, you will never respect the jabs and hooks from prospects that tell the truth with their wallet.

Or, if you are struggling with sales maybe it isn’t the fault of the product or the pricing, it may be time to rethink your sales team or their training, but that is a subject for a future posting in this series. Subscribe to this series, and we will cover that subject soon.

Header Image by Iván Tamás from Pixabay
The Pitch You Want To Give, Yet Need To Create

The Pitch You Want To Give, Yet Need To Create

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This post originally appeared on my company blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”. In this post, let’s talk about the challenge of doing a sales pitch for a product that has never been pitched.

Every day at a startup has challenges. You know this. That’s why being a founder or a member of the founding team can be very exciting. Having been in your shoes, I find that developing the sales pitch can be both heartbreaking and exciting. Starting from scratch and being ready to take on the world is noble, yet the downside is having absolutely no historical examples to jumpstart the creative process.

You may be lucky. Your software startup may be biting at the heels of one or more big competitors. If this is the case, you simply position yourself against their value proposition and say that you are better at something then the big guys.

Maybe you are also cheaper than the big guys (I hope not because pricing can always be lowered due to competitive pressures). Creating a value proposition that is “cheaper” may not be enough to differentiate you in the long run, but there is no question that it can be an advantage if your cost model still allows you to be profitable.

Do Not Internalize Doubt

But what if you need to create a unique value proposition and you cannot copy the value proposition of anyone else? What if your offering is so unique that it is hard to find another company and copy their idea?

First of all, if you are so unique that no one else is doing this, are you too unique? Is there anyone to actually sell to? Did you identify a missed goal that no one else can see, or is it a market that isn’t really there? Do you have a solution looking for a market, or are you in a market looking for a solution? This is really important, and I discuss it in my book, Eliminate Your Competition since competitors prove your need to be in the market. If you have no competitors, you may not have anyone to sell.

By the way, these questions come from many of my successes as well as failures. In my career, I have been fortunate to have amazing mentors. If you have them too, see if they can do a thirty-minute coffee break with you. Ask them your questions. They may not have the immediate answers you seek, but they will have encouraging words that may lead to somewhere you had not yet considered.

Another consideration is to find peer founders at your incubator or accelerator. An obvious cautionary tale, please rephrase your questions so as not to give away any intellectual property or competitive advantage. Polling your peers does have the advantage of boots-on-the-ground knowledge. Having founders who are in the thick of operations and execution will get you another perspective.

Do Something About It

Before your first customer order, you need to use the time-honored practice of A/B marketing. Whereas, my prior suggestion focused on opinion gathering, now I want you to put some of that knowledge into actual use. You should have enough material by this point to create a compelling story.

The downside of A/B sales pitches is that you run the risk of completely blowing a sales pitch to a prospect you desire. That is fine as it is almost as important to understand what NOT to say as it is to understand what you should say. After all, we all grok that “No” is never final and you can always go back to that rejection and explain that you didn’t explain it well and ask to speak again.

Once you have closed a few deals, then you need to have positive feedback from those early adopter customers. To ensure you are truly addressing a need that no other company is solving, you need customers to part with their precious cash in return for your product. Nothing else will prove your value proposition as well as cash.

After you have those first 5-10 customers, ask them what your value proposition should be for your company and product. They are probably not marketing folks with exceptional abilities to write concise and pointed value statements, but they can give you the essential words or philosophies. Hire a copywriter to take those basic statements to craft a message that is unique to you and epitomizes your message.

This method was recently discussed in an article on First Round. The article is about the email marketing success of Watsi. Grace Garey of Watsi explains: “For the longest time, we had it in our heads that people donate on Watsi because they are moved by a patient photo or story and they act on impulse. When we started to see droves of people sign up to donate continuously through the Universal Fund, we realized that users’ motivations were really varied and there might be new ways to reach them we hadn’t ever thought about. We didn’t expect that people really bought into a much broader vision for what Watsi was about — that they didn’t want to just help the person whose profile they were looking at, but underserved patients in general.”

Watsi found a value proposition for their fundraisers by listening to their donors (customers). They were able to learn from those successes to fine-tune their value proposition. You can do the exact same thing with your startup.

By the way, you should seriously check out Watsi. 100% of your donation funds life-changing surgery. It is a great organization, and you can donate here: https://watsi.org/crowdfunding. I don’t have any relationship with the charity, but I am seriously interested in making the world a better place.

Header image Photo by geralt (Pixabay)
January 2026
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