Bill FlynnAdvisor and operator for 20+ startups and counting

=Certified Gazelles Leadership Coach =9-time VP, WW Sales =GM,CMO - MindSHIFT, Online Services Division =Vistage Speaker Certified Predictive Index Practitioner Avid Jobs to be Done Promoter =Partner, JumpStart Resources, Temporary, outsourced mgt team for early founders

Recent Answers

I am a 10-time startup front-office Executive - Sales, Marketing, Service, etc. I would ask that you give more context to your question such as, are you a startup and still looking for a business model, are you scaling up and are trying to find the best strategy to dominate a market space? Are you in a new market space or in a crowded arena? The answer I would give depends greatly on the context of the situation.
Feel free to reach out to talk further. FWIW - I would not charge for that first conversation.


I am an 8 time VP, WW Sales for startups and 2 time CMO. In my experience, I agree with some of the other contributors. Your Marketing approach starts with your Core Customer that I like to define simply as:
1. The person/organization that you REALLY like working with,
2. Who REALLY likes working with you and,
3. Are your most profitable.

Here is a link to my most popular blog post on the subject to help you get started.

I provide 11 ways to use this info but once you have this it, you can also find many ways to market in terms of messaging, source, etc.

Good luck!


Here is a process (below) you can follow that comes from Lean Customer Development - author, Cindy Alvarez.

I have done hundreds of Customer Discovery (aka Product/Market fit) calls for about a half dozen startups I was involved in. It is more about your mindset more than anything. Think like a scientist. Do not try to prove that you are right. Try to disprove your hypothesis and if you cannot, you are likely on to something. You get into all sorts of cognitive biases if you go the other way.

Good luck - Bill

1. Try to have more than one person at the pre-calling session. Assumptions, hypothesis, target customer profile
2. Mind Map for idea
3. One sentence - create and share
Session work - Looking to get as specific as possible as it is easier to disprove versus something more generic
1. Identify your assumptions
1. Prompts to get started
* Customers have _______ problem
* Customers are willing to invest _______ to solve this problem
* Stakeholders involved in using/ buying this product are _______
* Partners involved in building/ distributing this product are _______
* Resources required in building/ servicing this product are _______
* If customers did not buy/ use our product, they would buy/ use _______
* Once customers are using our product, they will gain _______
* This problem affects our customers _______
* Customers are already using tools like _______
* Customer purchasing decisions are influenced by _______
* Customers have [job title] or [social identity]
* This product will be useful to our customers because _______
* Customers’ comfort level with technology is _______
* Customers’ comfort level with change is _______
* It will take _______ to build/ produce this product
* It will take _______ to get X customers or X% usage
2. Write your problem hypothesis - who, what, how much, when, and why.
* I believe [type of people] experience [type of problem] when doing [type of task]. or: I believe [type of people] experience [type of problem] because of [limit or constraint].
* Made up examples
* I believe that [tech operations teams] experience [wasted time and budget] when [predicting network bandwidth usage for their growing companies]. (Amazon S3) I believe [small businesses] experience [inability to grow their businesses] because [traditional email marketing platforms are too expensive and complicated]. (MailChimp)
* Helpful Hint
* Go Narrow
* One quick tip: All this talk about hypotheses being wrong might lead you to suppose that you should start with something broad and general. After all, if you don’t know much yet, why would you rule anything out? In short, speed. The more narrow your focus, the faster your progress. I state this explicitly because it’s the opposite of what most people expect. You might wonder, “If I start with a very specific profile, isn’t it more likely I’ll guess wrong?” Yes, but that’s OK. If you start with a very broad scope, you’ll find a huge amount of variation between individuals. You may end up doing 20, 30, or more interviews and still not be sure if you’re on the right path. Think about it this way: is it faster to disprove that cats like water or that animals like water?
3. Map your target customer profile
* What is the problem?
* Who is experiencing this problem?
* Draw opposing traits on the board (e.g.,Values cash versus values time, Prefers predictability versus Tries new things, Makes decisions versus follows orders, Low-tech versus tech-savvy, Low autonomy versus high autonomy Conservative corporate culture versus progressive corporate culture, Risk-averse versus risks are rewarded, Values stability versus values recoverability, Prefers turnkey solutions versus prefers best-of-breed pieces)
* Other questions to ask
* What does this person worry about the most?
* What successes or rewards does this person find the most motivating?
* What is this person’s job title or function?
* What social identity (teenager, mom, frequent business traveler, retiree, athlete, etc.) would this person use to describe herself?
4. Starter Questions
1. Tell me about the last time you ___.
2. What tools do you use for _____?
3. When you started using [x tool], what benefit were you expecting?
4. How do you solve this problem today?
5. If you could wave a magic wand and change anything about how you [perform this task], what would it be?
6. How important is this tool to reaching your goals/getting your job done?
7. What do you like most about this tool?
8. If you were designing this tool to solve the problem you described, what would you do?


My background is 10 startups over about 25 years. I am 6 for 10 in terms of outcomes (IPOs, acquistions). I suspect that my answer will not be what you expect. I am not sure that we are aligned that coming up with a business model is solely a creative process (that may be my inference). I have learned that you have to have many conversations with your customers that involve how they value your product, what outcomes they are looking to achieve and where your product and others do not completely satisfy the outcome(s) they are looking to achieve. You mention that you have spoken to many and have product/market fit. The devil is in the details on those conversations. I have personally had hundreds of Customer Discovery conversations and it took me a while to be proficient and effective at conducting them. I recommend that you revisit your current customers with the express intent to learn what the best business model is for you and them as well as how to learn your service design (not sure what you mean by that BTW) then you will be able to inform your creative process versus sitting in a room together guessing at what a good business model sounds like or what the optimal service design is. There will still be some guesswork, creativity, and experimentation but it should go much more smoothly, be more fun and move more quickly when you approach your customer and the problem with empathy, curiosity and compassion. That could inspire anyone who is truly in love with the problem! (versus the idea).

Good luck - Bill

One of the things that I provide to my clients, is to teach them how to run an effective meeting. I apologize now for answering a question with a question but I would be interested in the type of meeting or meetings you are referring to. Are these weekly leadership meetings, monthly meetings, quarterly planning meetings, annual strategy sessions? Each of these can be productive when applying the appropriate principals, however if you apply the principles of one to another they could be unproductive meetings . If you could be more specific, I can go beyond the generalities of be prepared, start on time, focus on important and significant first, make sure everyone is heard, etc.

Bill.- leadership coach

Dear anonymous,

I sm a multi-certified business coach, 30-year sales guy where I built/upgraded 8 teams as head of sales for as many startups. My answer is coming from a different perspective than the others. I have found that your question makes a number of assumptions that are important to state up front.

Assumption #1 - You have hired the best salespeople to sell your solution. They must be curious, empathetic and a great cultural fit - that is, they believe what you believe about what impact you are making in the world.

Assumption #2 - You have designed, developed and follow a proven sales playbook that continues to improve over time.

Assumption #3 - You have trained each to meet a minimum bar before they are autonomous.

Assumption #4 - You continually train them to improve in all aspects of the sales process - awareness, interest generation, qualification, needs analysis....closing and negotiating.

Assumption #5 - You hold them accountable for all of the above.

"Train (sales) people well enough so they can leave, treat them well enough so they don't want to" - Sir Richard Branson

This quote can guide you on next steps. The best salespeople I have come across are motivated by the intersection of money and fulfillment. If you hire, treat and train them well, the incentive plan will become obvious. As long as it also intersects the needs of the company, you have a winner or are at least approaching a winner.

My last bit of advice is to involve them in all of the above but do not ask them to solve the problem for you.

Feel free to reach out to talk further. No charge for the first call.


I suspect that I am going to offer a novel and likely controversial reply. Since you have lost 90% of market share and are in a newly competitive space, I recommend that you search for a unique and valuable position in the marketplace first. You certainly should apologize and make right to the degree that you can those that you have wronged but that does not necessarily mean they will or should be your customers in the future. I recommend that you talk to the 10% who are still with you and uncover or reconfirm a struggle that you can solve for them. If you do, I then recommend that you look at the the 90% to identify likely candidates for this new solution. The key for startups is to find a problem worth solving and then solve it in a way that helps a large enough market who are wiling to pay enough money for it to make a profitable business (and/or one you can sell). If you do this well, are empathetic and curious, your "brand" will begin to develop organically. I am happy to talk further if this short introduction is interesting to you as there is much more to this that you should look at internally first around Core Values, Purpose, etc. The long term aim is to find the intersection of your Passion and Purpose, what you do well and what customers want and value. Your brand is a by product of this. I have written a short blog post to possibly help you to start this process.

I think that Priyanka is on the right track. My advice is to first confirm that you are solving a problem worth solving for your target/core customer. That is, when you talk with them about your hypothesis, do enough of them say "Where have you been all my life? We have been searching for this solution for a while. We are so glad you are solving this problem for us."

Before you figure out if you are solving a problem worth solving, other than not running out of money, you should focus on nothing else. Please note that I did not say build a prototype or try to sell this a certain way. Stay focused on the problem (not the solution).

Here are some resources (books) you can look at to help you:

Will it Fly?
Nail it, then Scale it
Lean Customer Development

You Tube is also a great resource as there are tons of how to videos that can help you - Search for "Customer Development" or "Jobs to be Done" to get started.


My advice is always to consider how to increase profits versus revenue - "Revenue is vanity, profit is sanity and cash is king". I recommend that you figure out what your customers truly want and value. That will help you with either or both approaches of new versus existing customers. There are many ways to do this and I am happy to talk to you about these. However, a quick and easy way to get started is to do the following:
1. In a spreadsheet, created a list of recent customers that will likely have decent recall of the experience of working with you.
2. Create 3 additional columns to the right of those names
3. In one column, write "Customers we REALLY like working with".
4. In next column, write, "Customers that REALLY like working with us"
5. In the 3rd column put in the "Profit %" or whatever unit you use for profit by customer.
6. Order them by the ones that have both of the first two columns checked and then by profit - highest to lowest.
7. Eliminate all those that do not have both columns checked and those that have zero profit or less
8. Send a note to the top 10-20 customers on this list asking the following, "If you were to recommend us to a friend or colleague, what would you say to them as to why they should also work with us" or something similar to have them talk about what they want and value in your relationship.

This information can be most valuable in getting new business and/or increasing business with existing people. It also may surprise you as to why your customers buy from which can also unleash growth in many ways.

Good luck!


My answer is going to be counter to almost all of those provided. I have been involved directly (10) and indirectly (15) with startups over 25 years. I am also a student of business history and I get the sense that you do not yet know your target customer, nor if you are solving a problem worth solving nor if you are solving it in a way that enough people will pay you enough money to make a real business out of it. Unfortunately, too many founders start in the middle and hope everything will work out with belief and commitment. Ash Maurya has a great quote, "Life is too short to build something that no one wants." I recommend that you follow the Lean Customer Development method which means that you should not try to sell anyone right now. Go in with the mindset of discovery. I agree with one of the other answers that talks about empathy. That combined with curiosity are your best assets. If you go into trying to sell, you are not in the right frame of mind to learn as you will commit the ultimate sin in startups which is confirmation bias. I have several blog posts on my site that talk about this and recommend the following books - Lean Customer Development - Cindy Alvarez, Nail it, the Scale it - Nathan Furr or any videos from Ash Maurya, Justin Wilcox or anyone who is a disciple of Steve Blank.

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