Live, Personalized Advice for 100 Entrepreneurs – How can I help?

I have decided that one of my 2018 goals is to help 100 entrepreneurs.

I’ll try to make myself available for any entrepreneur, even internationally. That being said, my priority is to focus on minority and women entrepreneurs, as they are generally underrepresented in the startup community and are likely in a position to benefit the most from helpful advice.

The types of companies I am probably in a position best to assist are B2B (business to business) software companies. These are companies that sell their software, typically on a subscription basis, to other businesses. My specialty is more around mid-market and Fortune 1000 types of target customer profiles, and less so on no-touch/self-serve types of customers.

My qualifications include:

  • Formally advised multiple companies in the past on go-to-market strategies, including Palantir, RelateIQ (acquired by, Addepar, and others
  • Started two venture backed companies that have raised around $100M in combined capital
  • Ran the worldwide sales function for multiple organizations including carrying a $25M team sales quota
  • Personally met with 50% of the Fortune 1000
  • Interviewed about 1,000 sales people in the last 20 years
  • Hired 15 senior executives in the last 10 years

Topics I can usually help with include:

  • Getting your first 10 customers
  • Growing from 10 to 100 customers
  • Ideal customer profiles
  • Pricing and packaging
  • Deal negotiation
  • Hiring your first few sales people
  • Selling methodology and process
  • Venture capital strategies and tactics
  • Building your executive team
  • Executive compensation
  • Scaling your company from 10 to 100 employees
  • Building company brand and thought leadership
  • Goals and metrics
  • Company culture and values
  • Board communication

I think the best format for this work will be a 45 minute call, where we dive right into problem areas or issues you are dealing with. I will try to be as helpful as possible.

This “service” if you can call it that is entirely free. I am not looking for advising roles or anything beyond our initial call, as I unfortunately do not have time to do that. Now, they do say advice is worth what you pay for it. So keep that in mind…

I realize that starting a company is extraordinarily hard, and if I can even provide a little bit of help, even as a sounding board, it may ease some of the challenge in building your own business. That is not to say that I have all the answers, in fact, I am still learning every single day myself.

The only thing I ask for in return is that you comment on this page after I’ve provided my time and advice, and ideally mention the 1-2 areas that we focused on, so that I can keep track of hitting my goal of 100 conversations this year.

Ideamensch: Kris Duggan Interview

Author: Kris Duggan

1% better every day.

62 thoughts on “Live, Personalized Advice for 100 Entrepreneurs – How can I help?”

  1. I have been fortunate enough to receive advice from Kris on a few occasions. I can attest to his knowledge of developing customer profiles to go-to-market strategies to sales and marketing campaigns. It was through Kris’s guidance that I was able to kickoff my product marketing career.

    Thanks for all the help, Kris! You have undoubtedly been a positive influence on my career and life. Hope to see you on the track soon!

  2. It was eye-opening, yet simple advice from Kris to take a pause, go back to our prospects and actually ask and listen to their pain points, their expectations of a solution to solve their business issue, the perceived or real product gaps, and the price they’re willing to pay for the pain to be resolved. Given my company pivoted from a professional services offering to a SaaS solution in a new technology category, our customers, especially those we don’t win, will tell us why we didn’t win if we take the time to get feedback. Feedback is best solicited by our product team, or anyone not in sales, and to share the feedback with the team. It’s easy to get caught up spinning one’s wheels at breakneck speed; Everything becomes a blur. Slow down, revisit, learn and share.

    Great, and timely, advice. Thanks so much Kris! #priceless

  3. Great opportunity that every entrepreneur should take advantage of. A very impactful 30 minutes. We spoke with Kris for feedback on our GTM approach and the path to our first 10 enterprise customers.

    Kris listened carefully, asked specific questions and made sure he understood our situation. He was able to help reframe the stages of our GTM strategy, and key areas of focus. He was able to leverage his own experience to help us understand how to approach key stakeholders, and what kind of plan might make sense in the upcoming 6-12 months.

    Great, specific advice that is carefully considered and explained. Thanks for taking the time Kris!

  4. Going up the market is an ongoing challenge for almost all the SaaS companies, and there are not too many CEOs who have done that well multiple times. Kris is the one who has the experience, and also who is willing to spend his time to help other entrepreneurs to achieve that. I learned a lot from Kris on how to build GTM strategy for our enterprise segment, and he gave me both strategic and tactical advice that we can start executing on the same day.

    Highly recommend entrepreneurs to talk to him before he gets too busy 🙂

  5. Kris, thanks for the super valuable advice on how to navigate an in-person enterprise sales meeting for a 6 figure+ deal. We sought Kris to help us get advice on a pilot we were presenting to a very large customer. Kris helped us on how to really drive the meeting, how to build relationships with the attendees, gave us tips on how to plan for objections, how to get key decision makers to start thinking about our pilot as being a must-have for their company, along with many other things. Kris took his time to get a detailed understanding of our business and our specific scenario. Kris, thanks so much for taking the time to give us very detailed advice on the meeting we were going in to.

  6. My co-founder and I were connected to Kris for a 45 minute coaching session. We had an excellent time starting with him giving us a brief on his skills, listening to understand our business and immediately giving insightful feedback and recommendations. We found his feedback as candid as we could get and he showed not only a real enthusiasm towards the coaching session but a broad depth of knowledge across several aspects of start up businesses.

    We actually look forward to having more coaching sessions and advice from him as we found it very useful.

    Keep the good work up Kris!

  7. Kris is a sales genius! Always love getting advice from him on how to hire and incentivize salespeople, negotiating tactics particularly asking for your first million, and how to dissect a deal opportunity. Thanks Kris.

  8. Kris coached me for 45 minutes worth 45 hours of startup time, at least. He has very strong business acumen and offers sharp and immediately actionable insight. It’s not a session to just coach, it’s a session to act on right away.

    I walked away with the next steps for REveo’s growth with cohort testing via mobile messaging and analytics platform we use. Next step could be to refine revenue model upon learning. Looking forward to next session with actual data from our users.

    Thanks Kris!

  9. We had our 45 minute session today, and it was fantastic! I really loved the tactics and strategies discussed. We discussed a broad range of topics including go-to-market, sales comp, executive comp, product market fit and how to think about 2018 goals. I really hope no one else takes advantage of his offer so that I can take all of his time 🙂 Sometimes it’s just great to hear a little independent validation of your existing thoughts from someone as experienced as Kris.

  10. Kris has very strong business acumen. Already 5 mins into the conversation, Kris was able to understand what we do and was able to give valuable insights and guide the conversation in a direction that would be most beneficial for my business. We discussed positioning, fundraising and go-to-market. His thought-provoking comments and insights helped me align my thoughts better. I thank Kris for giving his valuable time. Hope I get to talk to him again!

  11. Kris is really chill! I am an entrepreneur who has questions re: venture capital strategies and tactics. Kris offered me valuable insights based on his first-hand experience. I was able figure out what’s the missing piece for preparing to approaching the VCs now. Thank you, Kris!

  12. This session was exactly what I’d hoped for — the perfect blend of probing questions mixed with guidance from a high-conviction, serial founder. In 40 minutes I took away several gems across pricing and packaging, scaling teams and product messaging. Appreciate your time and counsel, Kris.

  13. Kris was kind enough to offer his advice to me yesterday. As a first time CEO I talk to a lot of more experienced CEOs to try and learn faster and do better. The 45 minutes I spent talking with Kris was the most productive session I have had so far. He is candid, passionate and has been there and done it multiple times. Excited to see his new venture take off and I will be back for more guidance soon. Thanks Kris!

  14. Great meeting with Kris. Appreciated the detailed breakdown on how to go about testing market interest and field research, including key phrasing and framing of questions. Thanks, Kris!!

  15. I spoke with Kris for 45 minutes on our education startup. In 45 minutes, I learned more about packaging and pricing our fundraise than I had in probably my first two to three years in entrepreneurship. He has saved us a lot of time and resources from just the 45 minutes alone. He identified some new business model opportunities prompting us to run experiments with the new model. Kris is attentive, personable, and gets right down to improving your business. I am thankful for your time!

  16. Talked with Kris and I think the biggest help was his honesty and bluntness to the challenges we’re facing. If you read blogs or listen to podcasts on SaaS or entrepreneurship they brush over problems and issues with fairly vague advice and platitudes. Kris understood our situation very quickly and objectively went through each of our challenges in a thoughtful way, not trying to apply a formula – we discussed team hiring, ramp up periods for new reps as well as fundraising goals and how to best achieve them.

    If you can get on his calendar I would highly recommend!

  17. Kris was quick to identify our problem and provided solutions which were practical and achievable. His advise of creating a tiger team category was amazing. Keeping healthy pipeline by monitoring daily & weekly was basic yet extremely important in context of our situation. Thank you Kris, we appreciate your time.

  18. I appreciate the advice Kris gave me over our call. It is clear he has been through the same minefields before me and has some wonderful ways to navigate through them. We discussed hiring leaders, interview techniques, structuring sales teams, board composition and more. I would highly recommend connecting with Kris for an outside perspective. Thank you Kris!

  19. Kris was able to very quickly understand our SaaS product and the business model we have initiated. He is a great listener, asked good questions and within a very short time we were having a pretty high level discussion about scaling. Kris identified our personas and models and discussed the pros and cons of each. Our call ended with Kris suggesting a more focused approach, choosing one persona and model where we control many of the variables and can easily tell that story. He felt the chosen model was cleaner, more controllable, scalable and would make it easier for investors to see real value in the business quickly.

    Kris is clearly a pro at this. Quite a skill to speed date and be able to offer an understandable and meaningful suggestions at the end of only 45 minutes. Thanks, Kris!

  20. Kris and I worked together before when he ran sales at Socialtext. We had a great call. He provides a unique perspective on go to market and talking through the options was very helpful for Pingpad (TeamOps for Slack). If you’re starting something up, I’d strongly recommend you take advantage of Kris’ offer to have a call.

  21. Kris is a fantastic sounding board. He’s ‘been there, done that’ and provides a great perspective to debate hypotheses and strategic options. If you get the chance to talk with Kris – do it! It’s worth the time. Come prepared for a rapid fire discussion!

  22. The first time I spoke with Kris it was for pricing but it quickly became a conversation around sales, go-to-market and in general, customer development. Kris was able to hone in on the actual issue and gave advice on what we should be doing in a way that helped us think through how to approach our early customer base, pricing and business model. I just wish I had this conversation with him earlier!

  23. Kris has provided a refreshed view on our strategy after just spending a short while on a call with me. Very concrete and to the point. It’s clear that he has a “do-er” mentality and would be very valuable in a role of Advisor or a Board Member to any startup company.

  24. My conversation with Kris was immensely helpful. Within a few short minutes, he was able to identify potential hurdles and issues with some of the current business strategy and articulate a more sustainable growth approach for the business. He was able to leverage his vast experience to provide me with candid feedback, approaches and considerations that have already and will continue having a strong positive impact on me and my business. Thank you Kris!

  25. Kris is a very good listener. He was patient, allowed me to fully articulate what I was struggling with, and then jumped in with his thoughts. We mostly talked about positioning and crafting long term vision that would resonate with investors.

  26. It was great to connect with Kris. He offered his expertise on the space and gave a fresh perspective to our business. Often times, founders are stuck in their own bubble and it’s great to get a 3rd party opinion on our goto market, pricing, etc.

  27. Kris and I had a call and it was excellent. We discussed looking for early product market fit and he gave apt advice for the stage we’re in. It’s good to have a 3rd party sounding board, and even better when that 3rd party is experienced and patient. Very glad we were able to connect.

  28. Kris organized our sales roadmap in a plan that is going to drive huge growth for us. Having a 45min meeting with him was priceless. Thanks Kris!

  29. Kris was so generous with his time and provided great, tangible advice on how to move my consulting business forward and accelerate client adoption. I walked away from our call with a clear action plan and next steps. Thanks so much for your advice, Kris!

  30. Kris allowed me to think strategically and tactically. I came to Kris, brainstorming for ideas around running my own business, or continue in the corporate track. Instead, he brought to light that it could be the best of both. “Being an equity partner in an existing business can be just as rewarding and fruitful. The key is to continue the learning and gather ideas from other leaders/owners/founders. Ask and explore what other goals gaps can be fulfilled then meet that demand = a new business in the making”! So simple yet profound. Thanks Kris!

  31. Kris offered really practical and actionable recommendations as we think about scaling up customer acquisition and our positioning in the HR tech vertical. Really appreciated his insight into how we should be leveraging and expanding on current and prospective strategic partners in our space, as well as his willingness to offer help after our call together. Thank you so much for your time Kris!!

  32. Kris was able to effectively listen to my business strategy and give great advice on how to best position my product. He asked great questions and pushed me to start user testing way before finishing the product. Thanks again and I look forward to staying connected!

  33. Kris was exceptionally helpful in regards to our pricing and growth strategy. This is something that more successful entrepreneurs should do and I highly recommend taking him up on this invaluable offer!

  34. As entrepreneurs, it’s crucial to give ourselves regular reality checks to make sure we don’t waste our most previous resource – time. Kris is like… the ultimate reality check we can hope for. Through our conversation, he provided clear insights and suggestions to challenge our existing way of thinking. It was phenomenal! Thanks, Kris!

  35. As the CEO of, getting the chance to share my vision for the company, the hurdles I’m facing, and then have 45 minutes of back and forth of what to do next and the top 3-4 things to work on immediately – priceless! What we established:
    1) Build the team to deliver the $5M that we’re targeting to provide world class customer service, AND also be in position to grow in 2019. (Who is on the bus that should be, who shouldn’t be, who do we need).
    2) No need to raise capital – relying on cash flow is fine as is, Kris gave some amazing ideas on how to keep growing without the need for a raise.
    3) Clean up the cap table – he gave me some actionable ideas, introductions, and has “been there done that” where I haven’t.

    Kris saved me from future challenges, and added more value than I ever expected. Why invest 2-3 years failing in areas that you don’t need to fail in. Talk to Kris, ask him to help you – he’ll change your life!

  36. Kris and my brother Joe worked together at WebEx in 2005. My brother and I would often talk about business and he would tell me these great sales (war) stories that he and Kris had accomplished together. I met Kris a few years ago after my brother passed away unexpectedly. Kris wrote a heartfelt message on his blog that you can read below. Today I had a great 45 minute call with Kris. His experience helps entrepreneurs pull back from the weeds. Kris was able to quickly understand what I was trying to achieve in this new endeavor and gave me advice that helped me focus on the now. It’s easy to get lost in details that don’t produce revenue. Kris cut through the clutter in a matter of minutes and delivered options that I can use today. Thank you Kris for your time and commitment in giving back to the entrepreneur community. You are officially on my “Cool” list.

  37. Call with Kris was a great sounding board. Kris was able to understand what we do very quickly and was able to point out the market feedback we should be focusing on going forward. His comments and feedback on our go to market strategy and our messaging were to the point and well crafted. We have already started working on testing the suggestions. Thanks, Kris for taking time and helping us with your advice.

  38. Kris doesn’t sugarcoat any of his advice, and that’s what I appreciated the most out of our conversation. Straight and to the point, he was able to dissect what could be the reasons for the potential hurdles my startup was facing. I highly recommend scheduling some time on his calendar – his advice from his experience is priceless.

  39. Great call with Kris. I’m the first employee of a rapidly growing startup building out a BD team, and no one better than Kris – who has interviewed 1,000 sales execs – to brainstorm with. Advice included: 1) CEO should always be the company’s best SE, 2) when close to approaching product-market-fit (but not quite there yet), skew toward smart-savvy-creative folks with some selling knowledge vs. more experienced sellers, who will want a more turnkey process, 3) always be building pipeline with passive SE candidates. Kris also provided some great resources for ongoing coaching / mentorship including someone he deeply respects and also mentioned Thanks, Kris!

  40. Wow! That was the most valuable 45 minutes we have spent on the phone! Kris came prepared with an understanding of who we are and what we do, then he blew our minds with some heavy-duty insights that made it clear what our path should be. My co-founder and I are empowered and forever grateful!

  41. Priceless! Many of the advisory calls tend to be very high level and not get into the messy details of the problem. Kris gets you to unpack all the issues and helps you walk through a potential path forward which could lead to a definitive outcome. He patiently talked us through a new path which we are embarking upon and was extremely thoughtful about tactical advice. We can’t thank him enough for his time!

  42. I’ve met Kris several times since he started Badgeville and he’s always been genuinely nice and helpful. Rarely do you get the opportunity to have an extended conversation with an accomplished entrepreneur. Since he’s built and been involved with a number of successful businesses, he can provide insight irrespective of where you are in your own journey. He listened to our situation and offered candid feedback, including some concerns and doubts, some possible alternative points of view to explore, and practical goals to consider setting. If you are stuck in any way, I’d highly recommend you talk to him!

  43. I have known him for almost five years and Kris is truly the best! In this call, I had one of my other founders as well as a customer on this call. He cuts right to the chase and offers laser sharp actionable insights. We are going to use Kris’s suggestion for our positioning in the upcoming trade show. Our journey has just started to be another unicorn. Thanks Kris for the insightful and actionable advice! You rock, Kris!

    As for ourselves, we are SmartServ and we are the “Easiest & Most Affordable solution for Smart Contractors” 🙂

  44. Kris was super helpful and efficient. We looked at how to triple my sales by narrowing in on my focus. He was specific and direct, both of which were hugely helpful given how broad my service offerings are.

    The forced focus functions he suggested will go a long way.
    Thank you for taking the time!

  45. We had such an eye opening session with Kris. He right away understood our business and was well prepared. He had studied our webpage and emails I had sent him. He gave us valuable and concrete feedback. I really liked how he asked us questions and made us look at our business from different angels. He challenged us and at the same time gave us credit for what we had done so far. I also liked the way he made us set goals and how he clarified ways to reach them. Thanks Kris! Hope to be able to meet you again. Good luck with your own launch!

    Best wishes,
    Marianne and Kim
    Team Bobly

  46. I jumped at the chance to chat with Kris as he parlayed success on the sales side of the house into building the relationships necessary to start multiple companies. While I’m enjoying the journey of leading a sales org at a VC backed startup, I have bigger aspirations as my career progresses. Kris offered advice on how he made the transition from sales leader to CEO/Co-Founder and offered some perspective on how he knew the time was right to take a shot on his own. Additionally, he shared key learnings from his experience at Badgeville and BetterWorks that are relevant to many of the day to day challenges and opportunities I face today. Thanks Kris! – Ray

  47. I was fortunate to get some time with Kris recently. Our company is in the healthtech analytics space, and Kris had some fantastic perspective to share. We’re about to kick off a fundraising campaign, and his thoughts around our capital needs were both insightful and timely. I would highly recommend his counsel to other entrepreneurs. Kris, thanks so much for your time and insights. It was greatly appreciated.

    – Tom

  48. It is so generous of you, Kris, to provide your time like this. I have a Product Strategy consulting business and Kris helped me clearly see a number of converging datapoints on the packaging side of my service offering. His ideas and perspective as a CEO was very helpful and now I have a hypothesis to go test out. Thanks for the brainstorm Kris.

  49. What a great opportunity for myself and my partner to talk to Kris for 45 mins. We had sent a deck to him ahead of our call and it was clear he’d read this and given it thought before we spoke. We discussed pricing structure, marketing message, investment and signing up our first 10 customers. We really appreciated the comments and advice that Kris gave us. Very thought provoking and constructive.

    Thank you Kris for your time.

    I’d highly recommend this service if you can get on his calendar.

  50. Kris is a enterprise sales genius! His advice is precise and actionable which is the type of advice founders benefit the most from in my opinion. It’s great to see him spend some of his time educating less experienced founders on this topic.

  51. Kris rapidly understood my business and provided actionable, clear advice in a number of areas. It was an extremely helpful call!

  52. Kris was really helpful in discussing the caveats of growing everything at the same time after having raised a round of funding, and helping me prioritize. Particularly, Kris’ experience in building a sales team is invaluable. We also discussed the need to focus and not be sidetracked by shiny objects like partnerships, and how to deal with executive team mismatch. 45 minutes well spent!

  53. Kris was very earnest, respectful, and honest. Even though our field isn’t what he was familiar with, he still did his best to learn about the field and offer feedback and suggestions. Thanks for the help, Kris!

  54. Kris was so kind to schedule a call with me. I’m launching a new product and Kris was very helpful in confirming our approach and difficulties we’re confronting. He offered sound advice and particularly addressed the importance of tenacity and stamina and sticking with a goal until it becomes reality. It is easy to get discouraged with lack of follow up and interest from various contacts. However, if you believe in your product and have the passion, keep doing what you’re doing. It was very encouraging to hear Kris’s views and his own experiences.

  55. ‘Ridiculously efficient’ is the phrase that comes to mind when I think about our discussion with Kris. He is already thinking couple steps ahead. Applying massive “sales pattern recognition” experience, and evaluating positioning not just in the near term… but also relative to the competition and building moat. Super helpful and RARE to have someone who can deep dive into sales motions and pull-up with birds’ eye view into the future.

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