Goodbye, Squarespace

“Even when change is elective, it will disorient you. You may go through anxiety. You will miss aspects of your former life. It doesn’t matter. The trick is to know in advance of making any big change that you’re going to be thrown off your feet by it. So you prepare for this inevitable disorientation and steady yourself to get through it. Then you take the challenge, make the change, and achieve your dream.”

— Harvey Mackay

Twice in my career I've taken leave and found it difficult to return. The first time, when my son was born. The second, this past week. I was on Cape Cod for our annual holiday and felt really, truly present for my family in a way that I don't feel often enough. It also happened in Brazil when we went for the World Cup, so this has been a summer of reflection about what kind of dad I want to be and what kind of relationship I want my family to have with me.

When I joined Squarespace four years ago next week, Lila was four and Remy was weeks old (Kiki wasn't even an idea). All parents know that the one constant with your kids is that whether they are filling you with joy or driving you up a wall, it all goes very, very fast. Lila starts 3rd grade next year and is closer to a teenager than a toddler. A friend reminded me recently that work is a rubber ball and family a glass ball. The work ball can bounce. I am making the choice to go take care of my precious glass ball.

I am a builder, and Anthony and I have certainly had a productive four year relationship. From 24 employees to nearly 400. From modest revenue to double digit growth multiples. From a handful of engineers to marketing, HR, business intelligence, customer service, QA, dev evangelists, to a Super Bowl ad and beyond, all the pieces are now in place. I did my job: I built an organization and worked myself out of a job.

Of course, when you have an amazing product, it's much easier to be a successful businessman. I'm most proud of how we brought all our disciplines together – product, marketing, customer service – to deliver the unparalleled customer experience that drives our growth.

Next Adventure

Being a manager and being a founder's lieutenant have a lot in common. In my philosophy both are necessarily selfless and often unfortunately thankless. You elevate your people by putting their needs first, by devoting yourself to helping them meet their goals, by helping to define their ambition, and by providing them the support and coaching they require to be their best self. You derive your satisfaction from seeing others succeed, giving away the credit and the ideas, and sometimes taking the blame.

I love coaching people, and have a solid track record helping young companies frame their ideas and build their foundations. I've become a more active investor and advisor over the past 18 months and I plan on digging deep to help a few early stage companies cross the chasm. I've already got my first two projects lined up. If my nose for investment opportunity matches my ability to build and scale nascent businesses, then perhaps I have found my next calling.

Thank You Squarespace

Thanks first and foremost to Anthony, who has taught me so much, most importantly the power of focus and saying no. He turned this type-a multi-tasker into a rank-ordered list lover. To my team, who repeatedly showed me what passion and ingenuity were capable of and whose development and success fill me with pride. To my peers on our leadership team, who each challenged me to be my best self and taught me valuable lessons that will pay dividends in my future endeavours. And lastly to my friend John, who always returns my focus to the glass ball. Squarespace has been a wonderfully life-changing experience.

I'm long Squarespace. The team is remarkable, the product pipeline strong, and the leadership we brought in is what gives me the confidence to depart. I'm a proud shareholder that can't wait to see the company scale new heights.

The Best Cover Letter

Earlier this year I received the below letter. This may be the best cover letter I have ever received (that being said it's certainly not appropriate for everyone, nor every position). It is reprinted with the approval of the anonymous applicant. The original job posting is at the end of this page.

Don't let anyone tell you cover letters are BS. They aren't. I'm hard pressed to review a CV without a cover letter, and if the cover letter doesn't engage me, it's as if there wasn't one. Remember that I'm reading these all day long. You need to quickly convince me I should keep reading. You need to stand out. Your cover letter, like your CV, should be tantalizing, with personality and enough information to make me want to hear the rest of your story. Don't reveal everything about yourself yet. That's how you get the interview.

Personality alone isn't enough. The most common error folks make in writing a cover letter is to focus on why this particular opportunity is good for them. They write about their needs not the company's. The applicant should be thinking about their customer (me) instead. How are you going to help this company achieve its goals? What anecdotes from your experience are gonna convince me you are a real human who can make a real impact? Focus more on why the company needs you and less on why you need the company.

Last, but not least, proofread the shit out of your letter. Bad spelling and grammar are huge red flags. Misspellings of my name or the company's are too. If you can't pay attention to detail in your application what kind of faith can I have in your day-to-day work?

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February 23, 2014

Dear Reader,

I submit here my resume in consideration for the position of Director, Customer Care and Operations in Portland, OR.

While reading the 15th February OregonLive article on the spin-up of Squarespace operations in Portland I was intrigued by the critical stance the COO took on potential office space. Then after scoffing at the “How to Apply” section of the job posting, I let it percolate for a few hours then decided what the fuck. Here goes:

You will not find a better fit for the particulars of this job, as you've defined them, certainly not in a Portland native. Why? Because I started out and grew-up with the darling of the Silicon Valley all through the dot.com era; I was fire-hardened through many years living & working in Manhattan and now am barrel-aging in Portlandia. I’ve done stints in support, technical sales and management and I know what works and what doesn’t. I've built support programs & teams from the ground up.

I learned the art and ethic of customer service from John Doe at BigCo, in the early days, when those concepts still meant something there. John is from New York City and was my first-line manager & mentor then, and is the kind of New Yorker I came to truly admire later – hard & crunchy outside; soft & chewy inside. John always said “Treat the customer like you would treat your next-door neighbor – someone you might have to look in the eye every day”. I've stuck with that principal and built teams who subscribed and could live up to it as well. I may occasionally kick the shit out of vapid, incompetent and/or lazy salespeople, but I always treat the customer like gold.

Aside from the requisite industry bona-fides in my CV, I bring the following to the table:

• I will hook you up with the best Ashtanga instructor in Portland
• I'm certified as an instructor in the discipline of Rational Process and Problem Resolution and will teach it to the customer support staff and leadership
• I love MCM design, furniture and architecture and can consult on the PDX site-search (at least I can tell you if you are picking a dog and could do better)
• I have worked for two of the leading Contact Center infrastructure suppliers and have analyzed the others as competitors
• I don't suffer fools, slackers or whiners lightly
• John Doe is now SVP of Customer Care at BigCo 
• I am one funny mother-fucker

In closing, I'll just say that my resume probably looks a bit stodgy, but I'll be damned if I'm going to stuff it with bullshit fluffy language and credentials just to get matches on some HR filtering software and I'm not going to hire a 24 year-old career-coach to ‘teach’ me how to sell myself. I hope you like it anyway. I'll reveal my super power only if hired.

John Doe

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Director, Customer Care and Operations
Portland, OR

Squarespace prides itself on delivering exceptional customer experiences. In 2013 we were recognized by the Stevie Awards as the best customer service team in the country. That team will nearly triple in size this year, and we are opening a west coast office to complement our existing operations in New York and Dublin.

We are looking for a special person to establish this new customer care operation and immediately grow it 100 people per year for several years. You must be a seasoned leader with startup DNA and be a passionate advocate for customer care excellence. You also need to have a fun-filled personality well-suited to building office culture in line with our values, recruiting and retaining talent, and representing our brand in everything you do. This position reports to the VP, Customer Care.

Responsibilities

• Lead all local operations, with a primary focus on customer care, including hiring and staffing, monitoring staff performance, training and professional development, facilities, and HR
• Ensure our local office is truly a Squarespace office and all local operations meet and exceed the guidelines and standard determined by our New York HQ
• Drive cross-functional and cross-division relationships with stakeholders to ensure continuous improvements to the entire customer experience (includes communications, feature releases, support tool development, etc.)
• Focus on security and scalability of infrastructure and process to support exponential user demand; Help evaluate and advise on new technology and vendor reviews in contact center space
• Drive ongoing process improvement throughout the customer care team, with a particular focus on partnering with business intelligence to ensure data-driven decision making
• Produce KPI reporting and prepare action items for senior customer care leadership; Lead location communications with peer team and executive leadership
• Prepare insight-driven presentations for weekly team meeting, and facilitate team member’s presentations

Requirements

• 10-15 years experience, including minimum 8 years customer-facing experience inside a technology company’s customer care organization (preferably consumer SaaS or ecommerce), with meaningful exposure to senior leadership
• Broad experience managing, developing, and mentoring teams of 120 or more people, including experienced managers
• Experience building an operation from scratch a definite plus; Additional experience in retail or hospitality an added bonus
• Demonstrated expertise using data analytics and metrics to monitor, manage, and drive process and quality
• Comfortable working across disciplines including marketing, business intelligence, engineering, product, and business development to have a whole-business approach to customer care
• Ineffable ability to get stuff done; Comfortable with the workings of business operations such as HR and facilities
• Exceptional written and oral communication skills with an unyielding attention to detail
• Respect for the creative process, taste, and a passion for Squarespace
• A terrific sense of humor
• Portland native

How to Apply

A cover letter explaining why you love Squarespace, why this job is your destiny, and what your secret superpower is is required along with your CV.

About Squarespace

Squarespace mission is to provide creative tools that power the future of the web. From designers creating the next generation of web and mobile experiences, to anyone managing their own online presence for the first time, Squarespace provides elegant solutions that set new standards for online publishing. By focusing our efforts on the fusion of design and engineering, we strive to create long-lasting products that delight and surprise our customers.

Squarespace is defined by our insistence on providing an unparalleled user experience. All of our team members are charged with bringing creativity, honesty, and intellectual rigor to their responsibilities in a never-ending quest to delight our customers. We have high expectations of each other and work as a team to build things we are all proud of. That mindset, along with our execution, has allowed Squarespace to create revolutionary products and grow into the profitable business it is today.

Learn more at http://squarespace.com/about

You can accomplish anything

You can accomplish anything in life, provided that you do not mind who gets the credit. 

-Harry S. Truman

Fourteen Lessons

Concentrate on finding a big idea that will make an impact on the people  you want to influence.

Network intensely.

When you meet someone new, treat that person as a friend.

Read all the time.

Get enough sleep.

Evolve.

Travel extensively.

When meeting someone new, try to find out what formative experience  occurred in their lives before they were seventeen.

On philanthropy my approach is to try to relieve pain rather than spread  joy.

Younger people are naturally insecure and tend to overplay their  accomplishments.

Take the time to pat those who work for you on the back when they do  good work.

When someone extends a kindness to you write them a hand-written note,  not an e-mail.

At the beginning of every year think of ways you can do your job better      than you have ever done it before.

Never retire.

Byron Wien via VC Confidential

Core values

I just found these notes to myself. Wish I could remember where I wrote them down:

• Your brand is a lagging indicator of your culture. 
• The most successful companies have the strongest culture.
• All of these companies have a higher purpose. 
• Inspiration through vision and higher purpose makes motivation take care of itself.

And this:

• What are you willing to fire a superstar for?