LeadsCon 2019 Wrap Up

Well, it’s over. Four days in Las Vegas finds me reflective and proud. And, at least for the first few days upon returning, tired. Like, the kind of tired where you fall asleep at dinner. Or while helping with homework. Super, super tired. Given this, I waited a few days to draft my wrap up post for this event.

I’ve been attending LeadsCon for 10 years, so the Las Vegas event is equal parts reunion, brand-building, and business development for our clients and ourselves. This year, we saw more of that trend, with some adjustments here and there. Read on for a quick recap.

Partnership Marketing Workshop
We were fortunate to be chosen by LeadsCon and AccessIntelligence to lead a Partnership Marketing Workshop on Monday (prior to LeadsCon’s official kickoff). This event, our third in a row, has become an important anchor for our business. We look forward to it every year and commit significant (to us, anyway) resources to making it happen. This year, I was very proud of the effort. Among the high points, I’d include the following:

  1. This was our largest audience, to date. In fact, we filled the room.
  2. In addition to the audience size, we attracted the most diverse group we’ve ever had, with a particularly strong showing from brands and channel sale organizations. (This is very important to me, as without these folks actively engaged, things can get salesy, fast.)
  3. Our speakers did an amazing job keeping the audience engaged, and also staying real. In fact, our first session, led by Damon DeCrescenzo and Jason Kaplan from the Credit Pros, was as contentious and frictional as any I’ve seen. That’s what we aimed for!

There’s plenty more I could say about this event, but the above struck me the most.

Balling on a Budget
As a bootstrapped startup in an industry full of well-funded and established firms, we’ve got to be thoughtful about how we make a splash in Las Vegas. This year, we held a series of cocktail parties at our suites in the hotel. These were super fun, and they didn’t break the bank. For three consecutive nights, we hosted our clients, friends and partners. The venue was perfect, and everyone seemed to really enjoy it. And, we got to throw a party….every night!

Meetings off the Floor
While we were each active at the show and in the sessions, we used these same spaces as private meeting rooms, which worked out really well. These folks are always going hard, but I saw sixth gear from the team in Vegas. I think we took Anna to the point of critical illness, but at last check, she’s still among us and returning to normal. As is often the case, I’m blown away by the team’s effort in Vegas.

Innovation Seems to be Slowing
This is the only critical comment I’ll make, and I promise it’s constructive. When I walked the floor of the exhibition hall, it felt as if there are a large contingent of companies fitting into three buckets: networks, call centers, and software. The networks are buying and selling media, typically in a very transactional way. The call centers seemed hard pressed to differentiate. And the software companies appear to be locked in competition with one another on a product level.

None of the above is surprising, but it’s also a little disconcerting. I think there’s a lot of innovation left in this space, but sometimes, you couldn’t get a sense for that. I hope that next year, we see more innovation and disruption. It will keep the space vibrant, ya know?

That’s it from me. What an awesome week in Vegas!

Praise for Plymouth Rock

Yesterday, a firm we support did something that inspired us. While I typically don’t publicly point to our clients here on our blog or in a social media context, I’ll occasionally break from that trend when there’s a good enough reason to do so. This firm, and what they did yesterday, presents such an occasion. Read on.

Many Americans know of Plymouth Rock Assurance Company. For those in Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania, though, the relationship goes well beyond name recognition. There, Plymouth Rock is an institution, and one that our company is very proud to serve. That pride swelled a bit yesterday when I saw the news that Plymouth Rock had launched a comprehensive program to support its customers who have been impacted – and may soon be impacted again – by the government shutdown.

You can read the specifics, here, but I’ll summarize it for you: Plymouth Rock is allowing its impacted customers to pause their bill on existing policies and defer their down payment on any new policy. Further, they’ve announced that will not cancel those customers who cannot pay their bill as a direct result of the shutdown.

Forget your politics for a moment. That’s not what this is about. Instead, focus on the story of a company, a pretty big one at that, doing the right thing for its customers who are vulnerable to a scenario unfolding outside their own control. TSA Agents, air traffic controllers, Veteran’s Affairs (VA) personnel. Scientists and researchers. Parks and Museum workers. Law enforcement professionals. These are just a few examples of the folks who are being impacted.

Like many, I struggle to read through all the spin in the news, today. It’s hard to find a true signal amid the noise. But sometimes, someone does the right thing. When that happens, the news doesn’t need spin; it just needs to be shared. It needs to be acknowledged.

To our friends at Plymouth Rock: well done. And, thank you.

Strategic Partnership Workshop – Full Speaker and Format Announcement!

Strategic Partnership Workshop – Full Speaker and Format Announcement!

LeadsCon is less than two months away. Let that settle in. I’m guessing most of you still have holiday decorations up, and the biggest event in performance marketing is, like, right around the corner? Excited? Us, too.

We’re thrilled, actually, because we’ll be hosting a Strategic Partnership Workshop for the third consecutive year. This event, in particular, has become the cornerstone of our first quarter – we’re expecting a record turnout.

At this point, it feels timely to share some exciting and important details about the event. Our agenda and speaker roster are both finalized, and I’m confident that this year’s workshop will offer previous attendees and first-timers huge value. Attendees won’t just hear from a talented and diverse group of thought leaders; they will also be treated to an entirely unique format that we believe will help involve the entire audience in the discussion.

Here’s the full agenda:

Session 1: Unit Economic Spotlight: Achieving Better Commercial Outcomes Through Partnership

Our first session is meant to be a live wire. (In other words, we want it to get weird!) This will be a candid discussion about the true value of strategic partnerships in a direct response business. Many have experienced, first hand, the dissent that often exists between the business development and finance/operational leaders. We’re bringing this discussion to center stage, pairing two business partners who’ve grappled with the topic for years. Join Damon Decrescenzo and Jason Kaplan from The Credit Pros for a very real discussion on the commercial justifications of forming strategic partnerships.

Session 2: Forming, Developing and Executing a Partnership Strategy

We have three incredible panelists lined up to address critical phases to any successful partnership platform. But, in this setting, our panelists aren’t the stars – the audience is. The first half of this session will feature targeted breakout sessions, which will be headed up by our panelists. Will Curry from PureTalk Wireless will lead the group focusing on program strategy; Vince Lewis from Quicken’s Core Digital Media will cover prospecting, and Chrissy Ingalls from LightStream (SunTrust Bank’s innovative consumer lending business) will facilitate the discussion around program execution. These folks each boast tremendous backgrounds; merging this expertise with the audience’s perspective will, I think, be really cool.

Session 3: Group Mentality

Over the 10+ years since the first LeadsCon was held, our community has grown ever-more transactional. Publishers, networks and lead sellers all depend on paid media to create valuable inventory, while brands enjoy the convenience of per-lead (or, action) pricing formats. To maximize yield, competitive bidding formats have taken hold – pitting eager advertisers against one another and testing the limits of profitability.

But, what if brands and publishers could access customer populations through less competitive channels? Hundreds of millions of Americans each year join membership groups and associations, or participate in similar, brand-sponsored loyalty programs. In each case, the groups actively represent their members’ interests, often offering specialized products and services to their constituency. To better understand this ecosystem, and the dynamic relationship between affinity organizations and their brand partners, we’ve recruited two tremendously talented leaders from this ecosystem. Join Rita DiPalma from Augeo Affinity Marketing and Jason Nierman, who helped build TrueCar’s partnership program before spearheading Rollick Outdoor’s innovative partnership platform.

As you can tell from the above descriptions, we take this event very seriously. It’s critical that our audience walk away with real value from each of our sessions. If you’ve attended one of these events in the past, you’ll hopefully join us again. If you’ve not participated previously, please know how excited we’ll be to welcome you to this one. Here are the event location and time details:

Strategic Partnership Workshop

Monday, March 4
Mirage Hotel and Convention Center
Grand Ballroom D and E
8 AM – 12 PM

Registration Link: https://www.eiseverywhere.com/ereg/index.php?eventid=319804&
Discount Code: SPKR100 ($100 off current event pricing)

Why Write? A blog post about blogging.

I love to write. I try to spend a couple hours each week composing something with a goal of sharing my work. While I’m certainly not alone, I’m learning this is becoming an increasingly rare practice.

For example, not everyone on our team enjoys – or feels comfortable – writing. During our Q4 retreat (which happened a couple weeks ago), I asked a few of our folks what holds them back from writing more. “I’m not good at writing” was one reply (incorrect, by the way; this person writes beautifully). Others said they’re too busy. Some pointed to fear of public criticism, and not wanting to be vulnerable to that. The most common response, though, was that folks don’t know what to write about or what to say.

The discussion stuck with me. So, as I often do when a topic provokes extended curiosity, I thought I’d write about it.

I’ll start with why I write

I write, mostly, because I love to write. It makes me happy. I enjoy the process – from the planning and outlining to the refinement. It’s fun. And, admittedly, I get a little rush from the feedback that comes from posting something that people enjoy reading. I also like to try out new phrasing and messaging. I play with cadence and flow. I poke and I prod, so to speak.

For me, it started early – like, 5th or 6th grade. I was a wiry, goofy kid with ADD, but when I would read aloud the things I wrote in class, the other kids laughed with me (as opposed to ‘at’ me). That felt good, so I ran with it. Later, I developed an incredible relationship with Gregg Schwipps, who was my writing professor at DePauw. He taught me the value of authentic language and helped me understand how impactful a well-told story can be. That experience, like much of my time at the school, had a major impact on me. Since leaving college, and certainly since becoming an entrepreneur, I’ve always tried to keep some time in my schedule blocked off for writing.

Why writing is only sort of good for business

These days, I write a lot about our business. I do think it helps, but mostly in vaguely-attributable ways (at best). Others may point to revenue growth which is clearly linked to content, but for us, that’s not the goal. I don’t write to drum up business. It’s not that I don’t want more business – it’s just that I think content that aims to sell isn’t genuine. And, I think salesy writing that’s disguised as something else is obnoxious. I’m not saying that thoughtful content doesn’t sometimes lead to more business; I just don’t write with that as the goal. I’ve heard from several folks that something I’ve written has helped them to move forward. I’ve also been told that a blog post I wrote actually inspired someone not to become a client. Clearly, this wasn’t my goal, either!

Many say writing can be good for search engine optimization, but I’ve actually been told that mine isn’t. It’s well-documented that if you can assemble the right words in the right places in such a way that google likes it, this can be valuable. But, since this violates my first rule (don’t write just to drum up business), I think that kind of writing is annoying, too. Our former head of marketing, who I adore, once told me that my writing wasn’t ‘keyword rich’ enough. I don’t know the word for the sound your mouth makes when you hold your lips together and force air out, but that’s how I responded to him. (For an A/V example, Oklahoma State University’s football coach, Mike Gundy, famously made this noise during a press conference recently – it’s absolutely worth the distraction.)

Really, I think writing is good for business mostly because it helps you develop your business’s voice. It helps put a persona behind the brand. Writing allows you to assert a point of view. It lets your audience get to know your ‘vibe,’ or way of being. And it can help establish, I suppose, some authority on topics that matter to you or your audience. It helps you develop an answer to the question: ‘who are those people?’

Why non-marketing types should write, too

This touches back on my motivation for writing this post. I find it remarkable how few people outside of the marketing discipline publish content. Like, if you don’t have an MBA or the words ‘marketing’ or ‘content’ in your title, you shouldn’t write. I don’t get it.

I think business development and sales people, in particular, should write all the time. Think about this. You communicate for a living. Your job is to help people understand why they should work with you or buy your product. Unless you’re somehow pulling this off without the help of language, why wouldn’t you want to constantly improve your own use of words? When you go through the process of writing and posting something, you become more expert in concisely communicating your message. When it’s not just right, you can tweak in a way that you can’t do with spoken communication. Later, you can use those refinements in live action. Writing also helps you build your personal brand. It helps you chip away at the due diligence your audience is doing when you’re not in the room or on the phone. It establishes authority and authorship. It makes everything you say hold more meaning, and it helps you be seen as less subjective.

Some will say sales, marketing and business development are all so interconnected that this is last assertion is obvious. OK. We can debate that another time, but for now, let’s look at other disciplines. I love it when technical professionals write – especially when their work helps me make business sense of technical things. (For a brilliant technical view across a range of business concepts, I think HubSpot’s CTO and Co Founder, Dharmesh Shah is hard to beat.) Another example is finance and venture capital. While we’ve never gone the route of approaching investors, Los Angeles-based VC Mark Suster’s blog is some of my absolute favorite reading. And when I want to learn from content that can benefit my personal life, I often still prefer for those insights to make an impact on my business. I think Dr. Brene Brown – a research professor by trade – has absolutely made me better at home and at work.

Let’s land this plane.

I could go on and on. But, you’ll stop reading (if you haven’t, already). My point? You don’t have to be an expert in an area to have an impact within it. Sometimes, as noted above, content that aims to address one topic can help both the writer and the reader develop new thinking in other areas. In other words, don’t overthink it when it comes to putting your thoughts out there. Instead, open up. Write about stuff. Tweak it; play around with it. Then, share it. Even if you’re bashful about the value of your own ideas, you’ll benefit from the process. And, someone out there might just benefit from it, too.

Sharpen your pencil and share your ideas. You’ll be glad you did it.



From M/A to Partnerships: Understanding the important relationship between Mortgage Firms and Insurance Providers

A couple weeks ago, as thousands of professionals from within the mortgage and insurance categories flooded Las Vegas (for InsureTech Connect) and Boston (for LeadsCon’s Connect to Convert), a bombshell fell on the two industries which will surely impact business for years to come in each category. The news, in case you missed it, was the announcement of LendingTree’s (TREE) intention to purchase Seattle-based insurance lead seller QuoteWizard for north of $300 Million. (You can read the full report, here). On the surface, this deal makes a ton of sense. These two firms have independently done incredibly well in their primary markets; their joining forces should lead to even more impressive dominance in performance marketing space, with coverage in two of the most active and important lead generation industries.

Much of the work our firm does touches these industries – we represent leading players from both the insurance industry and the residential finance (mortgage, home improvement) ecosystem. In fact, we’ve been the driving force in a number of partnership programs between insurance providers and lenders. While we weren’t surprised by the news of the transaction, we do find it both extraordinary and noteworthy. I figured I’d write a little bit about the transaction, and more importantly, the general benefits of a mortgage-insurance partnership strategy.

First, though, some background. I know each of these businesses pretty well. My relationship with LendingTree dates back a number of years – I consider a number of folks on their senior team to be close friends. It’s a business that I respect tremendously. QuoteWizard has been a great partner to a number of the companies I’ve been involved with as well, and while their senior team typically communicates with my partner, Brett (our COO), I’ve come to similarly respect their work. These are good companies, and I’ve got exactly zero doubt that they’ve done something very smart by joining forces.

I’ve also believed for a long time that mortgage lenders and insurers make for very good partners. Dating back to Brett’s and my time at DoublePositive (when we launched the now-mothballed ReadyForMyQuote mobile product), I’ve been thinking about how to profitably align these industries. I’ve seen firsthand the success that USAA has had in helping their Members on both the bank side (which is where their mortgage products live) and the property and casualty business (I’m a Member and I’ve supported that business in the past). Later, at my last ‘real job’ (a national property and casualty insurance agency) we worked hard to partner with residential lenders. In other words, I’m a believer that mortgage customers make good insurance customers, too.

It would seem I’m not alone. This acquisition is certainly big news, but if you read the ‘trades,’ you know that there are a number of businesses out there who are thinking about insuring borrowers. Some are wholly-focused on this; these businesses exist specifically to leverage the relationship that these two industries can and should have. Others see this as a program or a channel – though not a business model. Whether all-in or simply playing at the margins, the list of firms looking to bridge the mortgage application and the insurance policy is growing. (Quick note: We represent some of these businesses, so I face a weird thing, here. I either mention just the ones we work with, share a broader list or just skip naming them, entirely. I’ll go with door number three to avoid any feather ruffling.)

So, why is this happening?
Given the level of activity between the insurance and mortgage industries, one’s mind naturally looks for the motivation behind this. Let’s put the acquisition that inspired this post on the shelf (as the parties involved may have had additional/different motivations than just the synergistic relationship these industries can have). I’ll focus instead on the perspective of a mortgage entity (which could be a direct lender, a broker, or even a loan officer) and the insurance provider (maybe a carrier, an agency or an agent). Specifically, I’ll try to nail down why they’re valuable to one another. To my mind, there are a couple major contributing factors, and then a bunch of secondary benefits. Both are briefly described below:

Major Factors
These industries are either critical or supplemental to one another’s ability to sell. You can’t borrow money for a home that isn’t insured. This means that for a mortgage firm to close a loan – and for a loan officer to get paid – an insurance certificate is required. (Further, RESPA mandates that the lender can’t sell insurance.) For the insurer, the relationship is less necessary than it is beneficial. I mean, who wouldn’t want to work leads who have to buy what you sell?

Secondary Benefits
There are likely dozens of solid justifications for lenders and insurance companies to work together. Some, though, are really simple and important; I’ll stick with these.

Insurance Benefits

Homeowners = better insurance customers.
While insurance carriers rely on dashboards that look like a nuclear submarine control panel, their profitability really comes down to just a few elements: acquisition cost, customer longevity, and products sold per customer frame the basics; loss ratios and claims frequency form the more advanced perspective. Working with homeowners aligns to better than index outcomes in each of these areas: they’re more likely to buy multiple products, less likely to move, and generally display a lesser risk profile than non-owners.

Exclusive leads rock! Cheap, really good ones are even better.
This actually speaks to the above point. Typically, when a mortgage firm refers its customers, it does so to a single, trusted entity. And, often, they do so without charging market rate for a lead. Insurance agents prefer exclusive leads to those they have to share with their competition. And because these leads don’t typically carry the weight of expensive media COGS (costs of goods sold), these programs can mitigate – or even eliminate – upfront acquisition costs.

Lender Benefits

Incremental Revenue.
Lenders have very few opportunities to engage their customers. If they’re successful in funding a mortgage, it’s likely years before they may be approached about a new loan (either purchase, refi or line of credit). Further, as consumers become more and more rate conscious, there’s no guarantee of that repeat business ever happening. Forming a partnership with an insurance company can mean incremental revenue for the lender.

Increased NPS and Loyalty.
Helping customers with things you don’t necessarily sell isn’t just good for revenue; it’s good for referral activity and loyalty. When a lender partners with an insurance company, and that partner delivers great service, it reflects well on the lender. They can expect an improved Net Promoter Score and a greater degree of customer loyalty.

Let’s wrap this up. LendingTree and QuoteWizard makes sense. So do the many business models and programs looking at the relationship between banks and insurers. To me, the more important message is that these programs aren’t just formed by acquisitions and deployed capital. There’s nothing stopping residential lenders and P/C insurers of all sizes from forming partnership programs that can leverage this value. These kinds of engagements help companies grow, but more importantly, they help customers have a better experience.

I hope you like this content. I’ve loved writing it. I think this stuff is fun to think about, but it’s even more fun to execute. I typically don’t use this blog to promote our business, but here I will:

If you’re a lender looking for an incredible insurance partner, we can help.

If you’re an insurance company looking for great lender partners, we can help.

If you have a technology that makes it easier for mortgage applicants to buy insurance, we can help.

Thanks for reading. Peace!

InsureTech Connect Recap

Our team has just returned from InsureTech Connect.

Whoa. What a week. For us, it was an incredible event and very much worth the trip. The content was very solid, and the networking proved to be a tremendous boost to the work we do for our clients. This post will bounce around a bit, as we covered a lot of ground over the five days we spent in Las Vegas. Read on!

It all began for us on Monday with the Strategic Partnership Workshop. Anyone who’s ever put on an event like this knows that very little goes completely as planned – such was the case for us on Monday. While it was a little hard for folks to find us, and then tough to hear us (AV issues), we persevered. And, we were thrilled to have a very engaged audience representing the full spectrum of thought leaders from throughout the insurtech ecosystem. Our speakers did a wonderful job going with the flow and sharing very meaningful insights. I’ve provided a quick review of each session, below:

Our first session was meant to feature Marc Buro from InsuraMatch and Abby Reddy from Quotacy. Well, one out of two ain’t bad – Marc came down with pneumonia and was unable to join us. Instead, Abby was joined by her partner, Jeremy Hallett, and Michael Babikian from Legacy Shield. They absolutely rocked. This discussion covered the importance of strategic partnerships when bringing an innovative and disruptive product to market. While we missed Marc, we were very lucky to have such a flexible group to kick us off.

Next, Daniel Weaver from Updater’s insurance group and Chad Lovell from Cross Country Home Services led a very informative session on the power of leveraging insurance-adjacent partnerships. This was a unique discussion in that it covered both ends of the unit economic equation for insurance marketers – Daniel talked about customer acquisition and Chad covered retention and claims mitigation. Great content from great folks!

We shifted our focus in the second half of the workshop to talk about how partnership-first firms fare in the market from an enterprise value perspective. We featured the stories of two recent acquisitions, with Brian Ocheltree from LeadCloud and Hal Schwartz from Quilt providing a firsthand account of their experience being acquired by larger enterprises. Brian spoke about the acquisition of his firm by National General Insurance Group and Hal told the story of being acquired by Mass Mutual’s Haven Life. For many in the audience, this was a powerfully relevant session – I credit each of these speakers for being extremely open about the process of building a business valuable enough to be acquired by major enterprises. It was a great discussion!

We then gained a different perspective on the investment and M/A process – this time from folks representing the capital side of that ecosystem. Ashish Dudani from Kiwi Tech and Grace Vandecruze from Grace Global Capital did an incredible job sharing their insights on how insurtech ventures can prepare themselves for capital investment and even acquisition. This discussion took an unexpected turn toward another important topic (and one that I couldn’t be more pleased to have discussed): diversity. Grace discussed the importance of having diverse backgrounds and thought perspectives at the board level, while Ashish spoke to this impact on the contributing team. The message, in each case, is very important.

Finally, we were fortunate to have a number of students present from Gamma Iota Sigma, the nation’s largest fraternal organization for the study of insurance-related curriculum in colleges and universities. GIS’s CEO, Noelle Codispoti, spoke about the organization and its mission. She even took a selfie!

With the workshop done, we shifted our focus to the show itself. For this event, we took a divide and conquer approach. While Brett and Anna carried the burden of a jam-packed schedule filled with partner meetings and introductory discussions, I focused on holding fewer meetings with principals of businesses we’ve been evaluating for partnerships with our clients. This proved useful for me – I learned a ton and was able to identify clear next steps on a number of key initiatives. Without the team being on hand to handle a massive number of earlier-stage discussions, I wouldn’t have been able to focus my own discussions in this way. I expect we’ll do more of this in the future.

It wasn’t all business. On Wednesday night we joined the 6,000 or so other attendees for the Salt and Peppa concert! We were all exhausted from four days of working in Vegas, but there was no way I was missing this. It was PACKED. The music was great. The people watching, though, was epic. I’ve never seen so many khaki pants (many pleated!) at a concert – and these people were absolutely jamming. It can’t be easy to get a few thousand insurance professionals to dance for two hours. Salt, Peppa and DJ Spindarella each have my admiration – they looked great and sounded even better!

Thursday was a travel day, but not before we held a client kickoff meeting that morning. I was impressed by the advances that Brett and Anna have made to this process, and really pleased to have completed the week with a kickoff. After this meeting, we made our way home – Anna to Santa Barbara and Brett and I back to Phoenix.

I’ll end with a note of thanks to the folks who lead InsureTech Connect. Jay Weintraub, Caribou Honig, Samarra Jaffe and the rest of the team did such a great job with this event. I’m so thankful to have been there and thrilled with the quality of the meetings we held. I can’t speak highly enough about InsureTech Connect and can’t wait to be there next year.

Task Management and Prioritization

Last week, I shared the opener to an ongoing series of blog posts on an important topic to me: Attention Deficit Disorder. (That first post really focused on sharing my story, which was important to me for a number of reasons.) I wrote about my motivations, which include sharing what’s worked for me in dealing with my own journey with ADD, particularly in a business setting.

This really kicks off that effort. I’ll begin with the thing that’s been hardest for me forever: task management and prioritization.

This is hard for everyone. For someone with ADD, though, it can be crippling. Together, deciding what needs to get done, when to do it and who should be responsible form the single most important element of my ADD management. And, while I’m writing from my own point of view, I hope this content can be helpful to anyone dealing with a complicated and busy work environment. (So even if you don’t lose your keys every morning or need constant reminding to take your dry cleaning in, you should totally still read this.)

By design, WorkBook6 is vulnerable to distraction. We represent the interests of dozens of companies. These companies pay us to keep them moving forward, and there’s always important work to be done. Deciding which tasks to take on, and for whom, is informed by a fluid field of context. As you might expect, keeping this all straight requires near-constant stewardship and sound decision-making. The process involves extensive communication with our team, our clients and our prospects.

Over time, I’ve come to understand what works best for me and establish a format that helps me to maintain progress across all facets of the business. My system is neither elegant nor complicated – with so many agendas in play, and with each having plenty of subtasks, I’ve learned that maintaining forward momentum demands simplicity. My task management strategy is thus, like, super-straightforward.

Before I do anything else, I run all new tasks through the same four questions:

  1. Should I (or we) do this at all? If this sounds simple, I’d challenge you to look back on the last 30 days of your own activity. Did you commit time and resources (either yours or your team’s) to tasks that didn’t have a measurably positive impact? What did you learn from that?
  2. What type of task is this? Is it revenue-impacting? Is it operational? Personal?
  3. Does this need to happen now, or later? Sound obvious? It’s not. Again, look back on the last 30 days. Have you committed yours or your team’s time to the completion of a task that, while useful, wasn’t timely? Did you do things prematurely? Again, what can you take from that experience?
  4. Should I do this myself, or would someone else be better? This one speaks to effective management. I’m frequently guilty of taking on too much, myself. Asking this question helps me recruit resources. My logic is simple: will this move forward more efficiently in my hands, or someone else’s? If it’s important that it gets done, the single most respectful thing I can do is be honest about who should carry it forward.

Once I’ve run my tasks through these questions, I put them where I can clearly see them, and organize them based on the conclusions I’ve drawn for them. My process is as follows:

  1. I write each task down on a post-it note (I prefer the Miami Collection from Post-It in 4” x 4”). I separate these by task type. Revenue-impacting tasks are written down on a green note; operational matters are always orange. Personal gets yellow.
  2. Next, I make two preliminary piles: one for the stuff that doesn’t need to happen right away and another for those tasks which demand immediate attention.
  3. I then separate each pile into two smaller ones (so I end up with four): one pile is for tasks that are best handled by someone else; the other is for tasks I’ll take personal accountability for completing.
  4. I stick the tasks on a four-quadrant grid which takes up on the southern wall of my office. This is my ‘big board.’ ‘Now’ and ‘Not Now’ form the x-axis; the y-axis contains the labels ‘Me’ and ‘Not Me’. To the left, I keep a little ‘Done’ pile. (This is recent – I used to throw the finished tasks away, but seeing a pile of completed tasks makes me feel good.) The whole setup ends up looking like this:

I follow some simple rules for distribution. I know that if I take on too much, personally, the system breaks down. So, the ‘Me’ tasks should never make up more than half of what the ‘Not Me’ ones. My thinking around timing is similar. If I try to do everything right now, the effect is the opposite – nothing gets done. So, I never let the ‘Now’ tasks make up more than half of the ‘Not Now’ items. This system allows me to make progress on what’s most urgent, and then re-prioritize items as I work through the backlog.

Another thing I’ve learned: when transparent, this process doesn’t only help me – it also provides a venue for building consensus. I practice transparency around this entire system, both internally and externally. I’m honest with our team and I ask for their guidance. I do the same with our clients. I ask them to help me prioritize the tasks we’re discussing. If a client sees a particular partnership as being critical, now, I agree to make that a priority. If I don’t think I’m the right person to complete the task, I share this as well. And if I get pushback on this, we discuss it openly. Sometimes I’m wrong. Other times, the instinct to delegate/collaborate is the right move. In either case, I’m grateful for the opportunity to land on the right direction, together.

This is my system. It’s not foolproof, but I’ve found that it works really well for me. Process wonks may view this as entirely too elementary. Many will point out that their business is way too complicated to fit into four quadrants, or that ‘not now’ is far too general a characterization. Right on, folks – do you. I’m half-crazy and what I do is not for everyone. But if you’re feeling overwhelmed, or scattered, you might want to try this out for a few weeks. If you do try this, let me know how it works out. I’d love to hear from you.

Thanks as always for reading. I hope this helps some folks!

Strategic Partnership Workshop – Full Speaker Announcement!

With InsureTech Connect now just a couple short weeks away, it feels timely to share more details on what we’re planning with our Strategic Partnership Workshop. At this point, our schedule and agenda are finalized, and I’m very happy with where we’ve landed. Attendees will hear from a talented and diverse group of thought leaders whose businesses touch the insurtech ecosystem in a variety of interesting ways. You can access the full agenda, here, but I’ve written a bit about each of our sessions, below:

We’ll begin with a discussion about growing profitably with a disruptive model – this discussion will feature senior executives from two insurance marketplace businesses: Abby Reddy from Quotacy and Marc Buro from InsuraMatch (part of the Plymouth Rock Assurance Company). I expect this session to be wonderfully informative for anyone working to solve for consumer choice and reduce friction in their customer acquisition funnel.

Next, we’re going to focus on insurance-adjacency and the potential this holds for improving customer acquisition, retention, and profitability. Daniel Weaver from Updater’s insurance division will speak to the ways insurance marketers can leverage high value audiences with a stated need for coverage. Chad Lovell from Cross Country Home Services (and formerly an executive with Liberty Mutual) will share important insights on the adjacency of home services to home insurance – and how a data and technology driven partnership within the connected home space can reduce claims and mitigate losses.

Because we believe that partnerships are central to the creation of enterprise value, it seemed logical to focus content on this. So our third and fourth sessions will do just that.

We’ll begin the perspective of founders whose partnership successes ultimately led to their acquisition. Brian Ocheltree from LeadCloud (acquired this year by National General Insurance) and Hal Schwartz from Quilt (also acquired this year by Mass Mutual) will help us all better understand the path to acquisition for a partnership-minded insurtech business. This will be a fantastic session for anyone leading or contributing to a startup, or folks who want to better partner with innovative new businesses.

Finally, we’ll look at partnership within this space from the investor’s perspective. This session – our last of the day, is designed to help us all better understand how capital views businesses which go to market through partnership. We’ll have two very unique perspectives to learn from: Grace Vandecruze, whose firm advises large insurance enterprises with regard to mergers and acquisitions, and Ashish Dudani, who runs an early-stage fund which invests in new insurance ventures.

But wait, there’s more! (I’ve been hoping to say/write this for a while – thanks for indulging me.) We’re delighted to welcome members of Gamma Iota Sigma, the nation’s largest fraternal organization serving students who plan to enter the insurance industry. These students are all part of a scholarship program announced earlier this year. We’ll even get to hear from the organization’s CEO, Noelle Codispot.

Seriously, folks, we’ve been working hard to bring forward a great agenda. As you can see, there’s a lot of content planned – and we’re going to deliver it all within a four-hour window. As a refresher, below are the details on this event:

Monday, October 1
1:00 – 5:00 PM
MGM Grand Rooms 203 and 204

If you haven’t yet registered for InsureTech Connect, you can do that, here.

If you have, but haven’t planned out the pre-day activities, I’d love for you to join us!

See you in Vegas! 

ADD – My Story

Like many in my field, I deal with Attention Deficit Disorder. Every day. Since second grade, when my parents and I sat in the principal’s office at my elementary school and were told that I’d be soon transferred into the special education program. (I’ll revisit this, later in this post.)

You may wonder why I would share this. Four reasons, really:

  1. I value vulnerability and there’s no shame in talking about mental health. ADD is core to who I am – why not discuss?
  2. I want to help people who, like me, live on the margins of ‘normal.’ I run a business. I help lead a family. I volunteer whenever I can. Just like everyone else, I figure out how to make it all work, but I do it while carrying a story that involves the word ‘disorder.’
  3. I believe that when properly channeled and supported, ADD is my super power. I may struggle to read my mail, remember my car keys in the morning, and keep my inbox at zero, but I also get to see things other, more organized people might miss.
  4. I want to share what works for me. And I want to hear from others what works for them. More specifically, I want to create content that covers how people in business can operate at an excellent level in a business environment while staying true to who we are as people.

Mostly, though, I just want to tell you my story.

Let’s go back to that meeting in the principal’s office. Old school. Fake wood paneling. Musty air from the swamp cooler. Citing the observation that I couldn’t read, my teacher and the principal sat with us and delivered the news that I was to be moved into the ‘portables’ – a collection of prefabricated buildings offset from the school where the special education program was housed.

My parents were blown away. I was actually an avid reader. My dad stood up, drove home (we lived a block away) and returned with one of my favorite fishing magazines.  I read from it for the group. Blank stares. Awkward silence. A bit of hand-wringing. In the end, their decision stood – if I was to remain at the school, I would do so within the confines of the special education program.

My folks pulled me out of the school, and enrolled me into a new, private school in the area. The Awakening Seed School featured small class sizes, a social learning environment. Best of all, they let kids’ passions inform their assignments. It was magnificently different. The founders – family friends to this day – were total hippies. We planted gardens and discussed global warming (well before it was a commonly discussed thing). I flourished.

We also visited a child psychologist, and then a psychiatrist. I was officially diagnosed and prescribed a new drug called Ritalin. I had officially become one of those ‘different kids.’

A.D.D. has been a dominant theme in my story ever since. I’m still haunted by the all-nighter with my parents the evening before report cards were to be sent home in sixth grade (I had turned in exactly zero assignments). Sports weren’t an outlet, yet, either – I’ll never forget the embarrassment of tackling my own team’s quarterback on the freshman football squad. And we still laugh about the look of shock on my parents faces when I brought home a far better than expected SAT score, despite my mediocre GPA at the one of the city’s lowest performing high schools. College presented new challenges, but also allowed for new successes. Work, as well. At each life stage, I’ve learned to leverage the unique tools that ADD provides me, and I’ve looked for support in the many areas where I’ve needed help.

I’ve also come to understand that at least in my case, this will never really go away. For me, that’s been more good than bad.

Thank you for reading this. In the future, I’ll be much, much more focused (ha!) about how I function with ADD in a business setting. I’ll cover organization, task management, stress reduction, team dynamics and likely much more. But first, I wanted to tell you my story.

Breaking Through (Part One): My (humbling-as-heck) lesson about inbound sales communication

Recently, I posted a joke about a trend I’d been seeing a lot on LinkedIn and in my email inbox. I wrote:

“Pro tip: if you’re hoping I’ll reply to your cold outreach email or linkedin message, maybe don’t start your message with ‘Dear Benton’”

Almost immediately, things got weird. Typically, a post like this might get a few likes, and a few hundred views. I didn’t use a hashtag, nor did I tag anyone. In other words, I wasn’t trying to get a bunch of views or create some sort of viral thing. I was just feeling sarcastic after receiving a bunch of impersonal, (I felt) poorly written sales pitches. Most of these came through LinkedIn, but plenty have guessed my email address and hit my inbox. Bad form, I thought. I’d had enough. I wasn’t prepared for what happened next.

That post, to date, has received over 15,000 views and has dozens of comments. Many responses were sympathetic – others who felt like these were mass-communicated, spaghetti-on-the-wall spam tactics. But a few folks pushed back, citing cultural differences and pointing out that my snark might be misguided. Others questioned my logic. “So what if it’s a mass communication, or a poorly written note? Aren’t you still limiting yourself from opportunity by not responding?” (I’m paraphrasing).

Whoa. This is some provocative stuff – these folks make some pretty good points. Many of us work in industries that are fairly agnostic to borders – is my bias toward a certain style, format or salutation actually holding me back? Am I being so snooty that I’m missing out on good opportunities? Worse yet, could this be an unintentional form of discrimination? I decided that I need to think more seriously about this.

I take this kind of thing personally. Introspection isn’t always easy. I hate discrimination and I despise unfairly biased thinking. I absolutely shudder to think I might be guilty of either. From a purely business perspective, if we’re missing opportunities for any reason, I had better get to the bottom it. I decided to conduct a little experiment.

I chose two messages that I wouldn’t normally entertain. Instead of ignoring them, I wrote a thoughtful response to each. The first was an inbound email, the seventh in a series of uninvited communications from an overseas firm looking to sell us on their services. The second was a LinkedIn message from a firm that builds explainer videos (the example they sent was about stem cells!). In each case I responded, saying that I typically don’t reply to such communications, but that I’d be happy to learn more. To the overseas firm, I offered a 15-minute call to learn about their product. To the LinkedIn message, I wrote that I’d received dozens of similar communications, and that I’d be interested in knowing what sets the sender’s firm apart, and also how they think they could help us. Here goes nothing, I thought. The results confirmed my hunch that I can and should do a better job of exploring inbound opportunities. Much, much better.

The overseas firm blew me away. No joke. The 15 minute call went 45 minutes. Then, I asked my partner to review it – he called it a ‘no brainer.’ He’s right – it’s got the potential to help our team in a number of ways. While I still maintain that they approached me in the wrong way, we’re definitely going to buy their product.

The firm that builds explainer videos fared worse. I got a canned message back with a list of giant enterprise examples (that have no reasonable connection to who we are or what we do). The sender suggested I talk to someone else in her organization if I was interested. Not impressed.

There’s a lot to learn, here. First off, I’m clearly guilty of not thinking deeply enough. I valued form over function – mostly due to being busy. Maybe that sounds like a tough pill to swallow, but I’m happy to have learned my lesson. We’re better for this humbling experience.

But what about the senders? Wouldn’t they benefit from some tweaking to improve their own efforts? I think so. This problem won’t be solved by expecting folks to look in the mirror and become more open to inbound sales pitches (though as I’ve experienced, we all should). There’s always room to improve, and for any business development or sales professional looking to break through the noise, there are better ways to get the prospect’s attention.

I’m going to tackle this topic in part 2, next week. Stay tuned!

Let’s Connect!