Back to…

I’m not in school any more, and as far as I can tell now, schools start before Labor Day for the most part, but it still feels like tomorrow is “back to school” for the working world. Business still hums along in August, and we’ve certainly had our hands full with one of the busiest months ever at Return Path, but somehow, the traditional end of the summer season still manages to have the trappings of a European August, with lots of people on vacation or doing more “work from home” days than usual.

As all that draws to a close today, at least for me personally, it’s Back to…lots of things:

– Back to New York! After a few weeks out of the city at our house in the mountains, it’s great to be back in Metropolis

– Back to shorter and more varied workouts! Training for my recent half marathon meant a lot of long runs and not much else. Now back to weights, pilates, elliptical, and swimming

– Back to more serious reading! I’ve read a bunch of trash over the summer. I was way overdue. My brain was starting to hurt. So I tuned out of almost all news, business books, and non-fiction for a month, and I plowed through enough murder mysteries to wallpaper a library (no doubt one populated by Colonel Mustard and Mrs. Peacock)

– Back to business! A few days and half days off and some working from home behind me, it’s time to gear up for a very busy September and October. Always busy months with industry events and pre-holiday retail client frenzy, this year will be even busier as we work to integrate our recent acquisition of Habeas as well as complete a number of other big initiatives

So happy Labor Day, which Wikipedia notes was created in 1882 and federalized in 1894 as “a day off for its working citizens.”

Angel Investors, Part II

A while back, I posted about angel investors and strategic investors, and the puts and takes of taking money from them as you start your business.  Tom Evslin has a great and much longer post today about finding and dealing with angel investors that’s worth a read if you’re giving any thought to this topic.

Taking Stock

Every year around this time, I take a few minutes to reflect on how the business is doing, on my goals and development plans, and on what I want to accomplish in the coming year.  Although most of that work is focused on how to move the business forward, I also make sure to take stock of my own career trajectory.  I always ask myself three questions when I do this:

1. Am I having fun at work?
2. Am I learning and growing as a professional?
3. Is my work financially rewarding enough, either in the short term or in the long term?

Of course, I always shoot for 3 YES responses.  Then I know my career is on track.  But as long as I get 2 YESses, then I feel like I’m in good shape, and I know which one to work on in the coming year.  I’m not sure I’ve ever had a situation in the dozen years of running Return Path where I’ve had 0 or 1 YESses.  If I did, I’d probably spend more time thinking about whether I was still in the right job for me.

I think these three questions can work for anyone, not just a CEO.  Hopefully everyone takes the time to take stock like this at least once a year.  It’s healthy for everyone’s career development.

If Only International Relations Were This Easy

Iceland is one of those weird places on earth where two continental plates meet — and you can see it. Here we are, me on the American plate and Mariquita on the Eurasian plate, with the earth seemingly coming apart at the seams in between.

If anyone’s interested in a short travelog to Iceland, here it is.

(This post, written by my co-founder Cathy Hawley, also appeared on Bolster.com)

The gig economy is a labor market where short-term or freelance roles are more prevalent than permanent positions. It’s generally characterized by having independent contractors rather than full-time positions, but in some locations and for some types of roles, gig workers may be part-time or fixed-term employees.

The gig economy that started with roles like artists, drivers and web designers is quickly expanding to include executive-level roles. There are  a few trends in today’s workplace that are driving this expansion. Startups and scaleups have more flexible, remote-friendly work environments and are looking for creative, less expensive ways of accelerating growth. Executives have shorter average job tenure and are more often displaced or between roles, and they are also interested in the flexibility that gig work can give them.

In a study conducted by MavenLink/Research Now, “The White Collar Gig Economy,” 47% of companies state they are looking to hire contractors to fill management and senior executive roles, including c-suite contractors. At the same time, 63% of full-time executives would switch to become a contractor, given the opportunity. These trends will be accelerated by the current economic downturn and recovery, as some companies have fewer resources, and more executives are displaced.

At the executive level, there are a few different types of roles that could be considered ‘gigs’. The most common two are coaching and project-based consulting.  Coaching or advising, and particularly CEO coaching and advising, has become very prevalent over the last 10 years. The CEO hires a coach who can help them navigate new situations and challenges. Often, CEO coaches stay with a CEO for a number of years, helping guide and support them through the stages of company growth. There are also coaches and advisors for other functional areas to provide similar support for other executives, although more commonly these coaches are hired for specific initiatives. 

Then there  is project-based consulting, where executive-level talent is hired to run a specific project such as reviewing a company’s packaging and pricing, performing due diligence on an acquisition, creating a Diversity, Equity and Inclusion strategy, or creating an investor deck for a fundraising event. This type of consulting isn’t new, and it’s similar to what large consulting firms offer. It seems to be more prevalent now for very senior roles than it ever has been in the past.

But the gig economy for executives now reaches well beyond coaches and consultants.  There are also executives who are hired into interim leadership roles while a company searches for a permanent placement. Some roles take a long time to find the right person, but there’s an urgent need for someone to take on the leadership mantle in the interim. If the interim executive is a good fit, and is open to it, it’s not uncommon for this individual to be considered for the permanent position.  “Try before you buy” works both ways — it can be good for the company and good for the executive, too.

An up-and-coming type of executive gig role is the fractional role. We are seeing this more and more in the last couple of years.  Fractional executives can either be consultants or employees, since the expectation is a long-term relationship, on a part-time basis. For example, 3 days or a certain number of hours per week. The fractional executive is responsible for all functional areas as a full-time executive in that same role. The company may be too small to need (or afford) their level of expertise on a full time basis, but needs more than just an advisor or project consultant. The fractional executive generally remains with a company until the company needs a full-time leader for that function, in which case either the fractional executive goes full-time, or the company hires someone new.  Fractional executives may support more than one client at a time, and may also come with a team of more junior functional experts who can support them to take on more work.

Finally, for our purposes at Bolster, joining a company’s board of directors could be considered taking a ‘gig’ role since it’s not a full-time executive role.  Startups and scaleups need independent directors, and their needs change based on their size, stage and strategy. We see a growing trend of companies contracting with directors for 1 -2 years rather than lifetime service. 

There’s a real opportunity right now for companies to capitalize on the expertise of this talent pool without having to hire them for long-term full time roles, and for executives who want to contribute their skills and expertise without the commitment of a 80-hour work week. Bolster is helping bring these two audiences together in a marketplace that matches on-demand executives with companies who need their services the most. Bolster also provides services for members so they can focus on their consulting rather than their business, and for companies to evaluate their executive teams and boards.

Back to Business?

Today is the day every year that everyone keeps saying, "well, it’s back to school time."  Ignore for a moment the fact that half of the schools I hear about now start in the middle of August…it’s interesting to see how some things in the business world really slow down in the summer, especially in August as well as the school system.

People really disappear for vacations, short and long.  Even if we aren’t like our European counterparts who really have it figured out and can virtually shut down in August, it’s just harder to get things done.  People might not all be out at the same time or for as long, but having one or two key people out any given week just makes it harder to make progress on things.

So, it’s time to get Back to Business.  September and October are the busiest months of the year in our industry with a packed conference schedule, planning cycles for next year, and the ever-present "holiday season" for our retail clients, so it should be a crazy fall!

Help Me, Help You

I’m conducting a really short reader survey about OnlyOnce.  There are about 10 questions, half about the blog, and half about reader demographics.  Please take 2 minutes to complete it for me so I know how I’m doing!  All responses are anonymous, as you’ll see.  Click here to go to the survey.

How Much Blogging is Too Much Blogging?

After being completely (and blissfully, I might add) offline for 11 days, I have returned to find 247 new postings in my Newsgator folder.  Only a short year ago, I would have come back from vacation to too many emails…now I get to sift through too many emails AND too many blog postings.

On the bright side, I have at least these two images of the Barolo wine country and the Amalfi coast solidly etched in my brain to ease re-entry to work. Anyone interested in a brief travelog of the Italian countryside, click here and follow the top link.

Boiling the Frog

We boiled the frog recently at Return Path. 

What the heck does this mean?  There was an old story, I’ve since been told apocryphal, we told a lot back when I was a management consultant trying to work on change management projects.  It was basically that:

If you throw a frog into a pot of boiling water, it will leap right back out.  But if you put a frog in a pot of water on the stove and then heat it up to boiling, you’ll boil the frog because it never quite realized that it’s being cooked until its muscles and brain are slightly too cooked to jump out.

How have we boiled the frog?  Two ways recently.  First, we let a staffing problem sneak up on us.  We were short one person in a critical area (accounting and business operations), and we had decided to try to go without the extra person for a month or two for cost-savings reasons.  Then, another person in that group unexpectedly left.  Then, another person in that group got seriously sick and was out for several weeks.  The result?  We were down three people in an area very quickly, without a proper pipeline of candidates coming in the door for any of the open positions.  So for a period of time, we can’t get the things done out of that group we want to get done, despite the heroic efforts of the remaining people in the group.

Second, we have had an Exchange server problem that has been plaguing one of our three offices for six months now (no, the irony of an email company having internal email problems isn’t lost on us).  In retrospect, the first time we had a big problem with it, we should have dropped everything, brought in an outside consultant, and done a rapid-fire infrastructure upgrade/replacement.  But we were truly boiled here — we kept thinking we’d fixed the problem, the situation kept deteriorating slowly enough to the point where the productivity of this one office was seriously compromised for a few weeks.  Happily, I can report this weekend that our IT team is cuting over to our new environment — "the promised land," as they call it.

How do you stop yourself from getting boiled?  I think you have to:

1. Recognize when you’re in a pot of water.  What areas of your company are so mission critical that they’re always at risk?  Have you done everything you can do to eliminate single points of failure? 

2. Recognize when someone turns on the burner.  Do you know the early-warning signs for all of these areas?  Can you really live without an extra person or two in that department?  Is it ok if that server doesn’t work quite right?

3. Recognize when you care about the frog.  You can’t solve all problems, all of the time.  Figuring out which ones need to be solved urgently vs. eventually vs. never is one of the most important roles a decision-maker in a company can make.

I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series.

I’ve always taken a few minutes at this time of the year to ask myself these four questions:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes, it’s time for a rethink of what I’m doing or how I’m doing it.

I was having lunch with my friend Bryton, the CEO of Aquabyte, a few weeks back, and that conversation spurred on a 5th question, which I’ll now add to my end of year routine:

• Am I excited about what I’m doing?

I’ve realized now that I’m over two years into the journey at Bolster that there’s a significant value in being really into the subject matter of the business. I thought I was at Return Path…but now I realize that I wasn’t nearly as excited about what I was doing as I could have been. Our work at Bolster of helping founders be more successful is more personally meaningful to me than solving email deliverability challenges. That work had real impact on the world…but I just wasn’t into it as much.

And that makes a big difference in answering the general question of “Am I on track?” at the end of the year. I’ll skip next week and see you all in 2023. Happy New Year and Happy Holidays, everyone!

How Deliverability is Like SEO and SEM for Email

I admit this is an imperfect analogy, and I’m sure many of my colleagues in the email industry are going to blanch at a comparison to search, but the reality is that email deliverability is still not well understood — and search engines are.  I hope that I can make a comparison here that will help you better understand what it really means to work on deliverability – they same way you understand what it means to work on search.

But before we get to that, let’s start with the language around deliverability which is still muddled.  I’d like to encourage everyone in the email industry to rally around more precise meanings.  Specifically I’d like propose that we start to use the term “inbox placement rate” or IPR, for short.  I think this better explains what marketers mean when they say “delivered” – because anywhere other than the inbox is not going to generate the kind of response that marketers need.  The problem with the term “delivered” is that it is usually used to mean “didn’t bounce.”  While that is a good metric to track, it does not tell you where the email lands.  Inbox placement rate, by contrast, is pretty straightforward: how much of the email you sent landed in the inbox of our customers and prospects?

Now let’s come back to how achieving a high inbox placement rate is like search.  If you run a web site, you certainly understand what SEO and SEM are, you care deeply about both, and you spend money on both to get them right.  Whether “organic” or “paid,” you want your site to show up as high as possible on the page at Google, Yahoo, Bing, whatever.  Both SEO and SEM drive success in your business, though in different ways.

The inbox is different and a far more fragmented place than search engines, but if you run an email program, you need to worry both about your “organic” inbox placement and your “paid” inbox placement.  If you are prone to loving acronyms you could call them OIP and PIP.

What’s the difference between the two?

With organic inbox placement, you are using technology and analytics to manage your email reputation, the underpinning of deliverability.  You are testing, tracking, and monitoring your outbound email.  Seeing where it lands – in the inbox, in the junk mail folder, or nowhere?  You are doing all this to optimize your inbox placement rate (IPR) — just as you work to optimize your page rank on search engines.  One of the ways you do this is by monitoring your email reputation (Sender Score) as a proxy for how likely you are to have your email filtered or blocked.  The more you manage all of these factors, the greater likelihood you will be placed in inboxes everywhere.

With paid inbox placement, you first have to qualify by having a strong email reputation.  Then you use payment to ensure inbox placement, and frequently other benefits like functioning images and links or access to rich media.  With this paid model, there’s no guarantee to inbox placement (don’t let anyone tell you otherwise), just like there’s no guarantee that you’ll be in the #1 position via paid search if someone outbids you.  But by paying, you are radically increasing the odds of inbox placement as well as adding other benefits.  There is one critical difference from search here, which is that you need good organic inbox placement in order to gain access to PIP.  You can’t just pay to play.

Like SEO, some organic deliverability work can and must be done in-house, but frequently it’s better to outsource to companies like Return Path to save costs and time, and to gain specific expertise.  Like SEM, paid deliverability inherently means you are working with third parties like our Return Path Certification program. 

As I said, it’s an imperfect analogy, but hopefully can help you better understand the strategies and services that are available to help you make the most of every email you send.