Phil O'Connell Menu


How I Increased Customer Engagement at Our Early-Stage Startup

My first experience in the startup community was right out of college.   One week after graduating I started as the first sales employee for Rentabilities.  I came into the position with limited sales experience and no startup experience.  Most of my learning at first was a process of trial and error, until I started using books, blogs and conversations over coffee to learn about how other people solved the problems I was facing.

At the time I didn’t recognize the larger set of responsibilities that came with the position.  I foolishly ignored account management and assumed the the normal day-to-day would keep our partners engaged enough to create the type of stickiness we needed to build a successful network.  It feels silly now, but at the time I didn’t consider the relationship would not be long-lasting without a good deal of maintenance on my end.

Over time our procedures became more fluid and effective, and had the long-term relationship in mind.  Here are some of the tactics we used to create engagement among our customers.

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One thing I quickly recognized was if I signed up a company and we didn’t start sending them business right away we would quickly be forgotten.  At it’s core the issue was engagement.  Because at that point our backend hadn’t been built to control the customer requests that came through our system there was no guarantee we would have business for them right away.  Occasionally I would call a company we had signed up as a partner and they didn’t even remember who we were!  We needed a workaround to create stickiness and make ourselves memorable without engineering hours.

We quickly solved the problem by sending new partners free t shirts and handwritten thank you notes.  I was already collecting their addresses when I signed them up, so I added one question about their shirt size to our conversation and started sending out our “Rentabilitees”.  From the very start I worked to make sure the experience of receiving our shirts was as high-touch as possible.

In almost all cases we would pay for quick shipping, which made the signup and gift a 1-2 punch.  We also made a point to get the softest and most comfortable shirts possible, despite the additional cost.  People called us and emailed all the time to let us know how surprised they were about the quality of the shirts, giving me another opportunity to collect feedback, update them on recent changes we’d made and get them excited for what was in our pipeline.

Also, every shirt came with a handwritten note from a team member (normally me) referencing what we had talked about on the phone to make sure it was truly personalized.  That level of personalization only worked because of the in-depth conversations I had with these customers.  In my first year I signed up over 500 clients and nobody got the same note.  I began having extremely long and personal conversations to make sure I had something personal to mention in my note.  These longer, more personal conversations created additional engagement in and of themselves.  It was, as Michael Scott would put it, a “win-win-win”.

I would send shirts for more than just the decision-maker.  I would offer shirts to the receptionists, coworkers, spouses, and even their children if they came up in our conversations.  (We even went so far as to have a pink onesie for a baby made at one point.)  This unexpected generosity was something our partners commented on frequently.  I included my business card in each letter to make sure they had my contact info and felt comfortable calling me.  Many partners used that contact info to call and say thank you as soon as the shirts arrived.  We even had companies offer to have their delivery teams wear matching Rentabilitees when delivering to customers they met through our site.  The response was tremendous.

Lastly, the dev team helped to make things social by setting up a “secret” page on our site where we’d post photos of our partners wearing their shirts at home or when they travelled.  This created a social element that engaged our audience and reinforced the sense that they were joining a community.  Our mindset was never that we were just bringing some rental companies extra customers, but that we were taking the rental process online in a way that benefitted both customers and rental companies.  To physically show them other suppliers around the company that were also on board with our movement made it much easier to pass along our mentality.



Keeping up with a large number of business partners is extremely difficult.  At the end of my first year with Rentabilities I had signed on over 500 partners and was fully responsible for maintaining those relationships.  Working for any early-stage company is an exercise in controlling the chaos, and finding time to stay in touch with these people was no exception.

For many partners I maintained regular contact in my day-to-day workflow.  For our other partners I had to schedule periodic check-ins.  The points of contact at these companies needed to hear from me to keep them engaged, though sometimes I just didn’t have any good reason to call.

It’s really difficult to call a company you’ve underwhelmed, but it’s a perfect way to make sure your feedback is well-rounded.  If nothing else, their frustration can lead to some extremely candid feedback.  People who are unimpressed don’t pull punches, and some of the best feedback I received was from calling companies to check in and admitting our relationship has not been as fruitful as I had predicted.  In the end, having the courage to call and let them know I was thinking about them and how to serve them better sent the right message.  It also gave me a chance to explain what was in our pipeline that would help us deliver on my promises.

I remember getting great feedback from a man in Texas named Karl.  I called and admitted we hadn’t sent him the volume of business we had hoped we could.  I explained his location made it tough to send him business because we focused on top cities, and that we couldn’t control the pricing his competitors listed on our site.

Karl admitted he was frustrated but still took the time to give us detailed feedback about his use case on our site.  He explained why certain upcoming features were going to be ineffective and kept us from wasting valuable time building unnecessary functionality.  He also gave me insight into how we could create value for providers outside of the cities with top demand on our site.

In the end his recommendation saved the dev team serious time and helped us serve hundreds of partners that would have felt marginalized like he had.  If having nothing good to say kept me from picking up the phone he would not have stayed engaged or given us that important feedback.  In the end that feedback came full circle and helped us to make him one of our top partners nationwide.



At any startup the feedback loop needs to be an essential part of the growth process.  It should factor into every major decision and iteration.  Because feedback is so strongly tied to success it makes sense to collect feedback whenever possible.  A great way to make sure that partners continued to take the time to give feedback was to take things full circle and let our partners know exactly how their specific feedback had influenced what we built.

This process substantially boosted engagement among our partners.  I made a point of tracking who gave us our most important feedback and then reached out once that feedback was baked into improvements to explain that their feedback was directly responsible for a decision we made.

For a startup employee news about feedback being considered and acted upon might be unsurprising, but for the average person it’s very exciting to know your opinion matters.  It was always a great call to make because people were so happy and proud to have been a part of our process.

My personal strategy for notifying people about us using their feedback was to send a very short email saying what happened.  I would give very little information and end the email with my direct phone number and a suggestion to call if they want more details.  I’ve received call backs almost instantly by excited customers wanting to know all about it.  I would even send the email before updates happened to make it seem like an exclusive sneak peek at our upcoming changes.


“Hey Andy!

Thanks for your feedback last weekend!  I remember you were busy with your family so it meant a lot.

I brought what you said about our notifications system to the design team and they just showed me their next update.  Your feedback factored heavily into the new system they’ll be launching tomorrow.  You should recognize what I mean when you use the site!

I’d be happy to connect about how your feedback factored into the design.  My contact info is below my signature.


An email like that normally earned me a phone call.  There was never once a negative reaction to this.  It reinforced that we valued their opinions, that we remember them individually among all of our clients, and that we are constantly making improvements to our system.  It also gave me yet another opportunity to collect feedback and the personal contact strengthened our professional relationship, helping to 
create customer champions.



When calling leads it was very difficult to get through to decision-makers.  Rental is a seasonal business.  Outside of the summer busy season the company owners or managers were frequently not around, sometimes running their business through voicemails for months at a time.  During the busy season it was a challenge to get even three minutes of their time and attention. That meant repeatedly talking to receptionists, answering services, distant relatives employed through nepotism and all manner of people in-between.  I began to recognize that not only was the first impression make-or-break, but that I had first impressions to make with each person I talked to on the way up to the company owner.

Quite simply, if the first person to pick up the phone doesn’t like you they have no incentive to put you in touch with their boss.  I also had to deal with the person on the front line summarizing the reason for my call.  That meant whatever I said to the initial employee was filtered through them and potentially through their lack of context, disinterest, or lack of time.  In that way the first person I talked to either set me up for failure or success, making the first impression with that person just as important as the first impression with their superior.

By going well out of my way to treat everyone along the line with respect and genuine interest I was able to make real connections with multiple points of contact at each company.  Those connections created engagement, which paid back handsomely.  I found that while I needed to work my way up to the boss to initially get the decision about a partnership, after the decision the ones using our system on a daily basis would frequently be the same receptionists and assistants that I had spoken to in the first place.  Because I had not treated them as stepping stones to their bosses but as an important and meaningful connections it set them up as happy and engaged users of our product.


Being memorable should be common sense, but it’s worth explaining a strategy for this.  In each conversation I would try to ask a question the person I was talking to hadn’t heard before.  In addition to making my days more interesting it sparked conversations that helped me connect with people on a personal level, creating more engagement among our partners and in turn benefiting us as well.

An excellent example is Steve in Tennessee.  When we first onboarded his company he was just one of hundreds of partners I had signed on.  At first Steve was unengaged.  He didn’t see our system bringing him extra business right off the bat and wasn’t quick to respond to the customers we matched him with.

However, everything changed one day when, searching for a new and unusual question, I asked him how unpredictable weather factored into his business.  Steve had a lot to say about the topic, (and being in Massachusetts made it extremely easy for me to participate in a conversation about unpredictable weather.)  When I mentioned we were in Downtown Boston Steve got excited.  Steve explained to me he had lived here for years, going to Berklee College of Music and supporting himself waiting tables at the Union Oyster House (two blocks from our office).  We started talking about Boston and about music (a mutual interest of ours), and would touch on those two things every time we connected.

That conversation was the exact point at which we turned a corner.  For the next ~18 months every time we needed feedback on a new offering or feature Steve was one of my first calls.  Even if we hadn’t sent him much business recently he was still willing to give me a half hour or more of his time to put me in the mindset of a small business owner.  He was full of great advice and pulled no punches in explaining rental regulations, time constraints, and even expected laziness among our partners.  By the time we closed up shop Steve’s company had one of the smallest deal sizes among our partners nationwide, but because of the question I asked in an attempt to be memorable we were able to create a lasting relationship that turned into extremely valuable feedback for us.

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Have you struggled with engaging your customers and holding their interest?  Do you ever have to deal with customers that you just haven’t been able to deliver to? If so, what are some of your strategies?  Please share in the comments section below.

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Is the Problem You Solve (Still) Important to Your Customers?

The basis of any successful startup should be that it solves a problem that matters to potential users.  It’s even become part of startup terminology to ask people what problem they are solving when figuring out what their company does.  The terminology only serves to reinforce the reasoning that if what you’re working on is not a problem to someone it’s not worth working on.

When deciding whether to pursue an opportunity it’s important to figure out how important the problem is and who it matters to, and don’t think the work stops there.  During the lifespan of your company it’s important to periodically reassess whether your initial findings about the problem were correct.  Consider whether the research was thorough enough and whether the thoughts your customers have about your product or service have changed since you started the company.

Continue reading…

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Why Your Startup Will Die Without Customer Champions

championHi there!  This is my first blog post in a series of three posts discussing how customers can be champions for your company.  Topics covered will include why they are important, how to identify them, how to give them preferential treatment, and more.

Tentatively, the three posts will be as follows:

#1 Why Your Startup Will Die Without Customer Champions

#2 Identifying Your Customer Champions (and How to Treat Them Differently)

#3 Customer Satisfaction is Bull****, Customer Loyalty is Priceless

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#1 Why Your Startup Will Die Without Customer Champions


Who are your most important customers?  When you decide which are most important are you choosing based on deal size, how long they’ve been using your platform, or maybe their potential to increase spending?  How about whether their name rings a bell with consumers or whether they’re worthy of namedropping while doing press?


If those types of characteristics define your most important customers you aren’t necessarily wrong, but I suggest stepping back and looking at things from a different perspective.  I believe that in any startup your most important customers are those that are willing to be a champion for your cause.  When they go out of their way to spread your gospel these customers instantly become extremely important to your organization, regardless of traditional measures of importance.


If you aren’t yet sold, consider that a customer champion is the gift that keeps on giving.  A champion is a person or a whole company who is willing to go out of their way to be an advocate for your product or service.  These are the people you call when you need feedback on a new offering.  They are the ones you ask to give reviews for your landing page.  They are the ones who call friends in their industry and talk up your company.  Most importantly, in the earliest stages of your startup each of these benefits are exponentially more impactful.  That feedback helps you avoid iceberg-sized issues that would otherwise sink your drastically undermanned ship. Those reviews are the ones that catch eyes and lend credibility to your product.  These champions have the ability to spread your gospel to industry peers who would otherwise ignore you, and that word of mouth can take your network to critical mass.


Your startup will die without these  advocates for your brand.  Consider them a key to your success.


When I think of our customer champions during my recent role in a rental marketplace called Rentabilities I actually remember many of those client relationships were plagued with complications.  Many companies that were extremely enthusiastic about our startup had a series of issues with the marketplace that were embarrassing and regrettable.  Some of these companies caught our site when it was down for maintenance or were accidentally mass emailed.  The fact that we had those issues with our champions seemed like terrible luck at first.  At the time I would have preferred to burn a bridge with a company that was only mildly interested in our site over having any issues with a champion.


In hindsight I was able to see those experiences were part of what made those customers so special.  It’s not that they were people whose nature was to forgive and forget.  They dismissed our errors because they had enough faith in what we were doing to understand that anything disruptive is going to encounter setbacks.


I was racking my brain for the perfect example of a customer interaction that could explain how our company would have died without their support.  I realized the best example actually came shortly before I joined the company.  It came before any sales were made and before before the site was even live.  The champions were three local rental companies that allowed the founders to spend time in their stores, observing their operation.  They explained to the founders what was important to them as business owners, what their customers cared about, what their pain points were, and whether there was even any need for the process of renting to be brought online.  One company even cared enough to let the founders use space above his rental store as an office, becoming the ultimate champion for our cause.


Without that critical time of research Rentabilities would never have fully launched.  If we were forced to fine tune our marketplace over time based on complete trial and error we could not have created an experience that other companies wanted to be champions of.  We never would have even gotten off of the ground without those three initial champions.

Does your startup have champions?  Do you consider them to be your most important customers?  If not, why?  If so, I’d love to hear your thoughts in the comments below.


  • Aldo Beqiraj

    “They explained to the founders what was important to them as business owners, ***what their customers cared about***, what their pain points were, and whether there was even any need for the process of renting to be brought online.”

    Absolutely agreed. Insight from your customer’s customers is essential. They know them best and will always point you in the right direction when you are in the developing stages of your business model.

  • Phil O'Connell

    Thanks for reading, Aldo! It’s always good to see that founders aren’t scared to take on the grunt work of collecting customer feedback.

    Good luck with Bringrr.

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