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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?

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 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

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.


  • 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


  • 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


Which would you prefer?


"Thank you"

3 Notes

The Early Stage: There Are No Crowdfunding Secrets


I’ve spent a lot of time lately thinking about crowdfunding strategies and, judging by the number of “Secrets of Crowdfunding” posts and expert talks out there, I’m not the only one trying to figure out how to crack this nut. (I’m one of the few, however, who’s trying to make a business of it.)…

9 Notes

Dribbble Blog: Squarespace 6 Rebound Playoff


We’ve teamed up with our friends over at Squarespace to celebrate the release of the all-new version of their fantastic website building service. The official Squarespace Rebound Playoff kicked off last Thursday and has already racked up 200 rebounds of, dare we say, some incredibly…


The Euro

I received this interesting note from a friend last week, part of an ongoing discussion about the Euro and how it may affect the American election:

So what lies ahead for Europe? A bearish scenario with a substantial cheapening of the Euro vs the UKPound and vs the USD followed by the beginnings of a classic Europe-wide inflation? Or a bullish scenario: recovery and growth of the economies and increases in their rates of employment? I’m not bullish, are you? My concern about applying what sounds like a US-type solution to the European problem is that the US has the advantage of a unified set of laws affecting both its singular US banking system and its singular and unified economy (an economy that produces the unique powerhouse that is the US gdp). I can’t see how they can make an economic whole out of an economic patchwork quilt (without a brand new unifying political structure). It will forever look like a work in progress, not like finished goods. The US experience with its First Bank of the United States a couple hundred years ago is evidence of that. 

1 Notes

The Cause of His Life (or Thank You, Massachusetts)

Dear God, please save journalism.​

"Mandate struck down — High court finds measure unconstitutional."  — CNN

"Supreme Court finds health care individual mandate unconstitutional."  — Fox News

​First, the QOTD, from Josh Marshall.

"This is an imperfect law. But what’s most important is that it provides a structure under which the country can make a start not only on universal coverage — as an ethical imperative — but on doing away with the waste and inefficiencies created by the chronic market failure of the US health insurance system. Again, that matters. And I suspect that there’s no going back."  — Josh Marshall

​Now for the right wingnut machine…

"Today, in a closed door House GOP meeting Thursday, Indiana congressman and gubernatorial candidate Mike Pence likened the Supreme Court’s ruling upholding the Democratic health care law to the Sept. 11 terrorist attacks, according to several sources present."  — Politico

What else fun happened?

"If government can mandate that I pay for something I don’t want, then what is beyond its power? If the Supreme Court’s decision Thursday paves the way for unprecedented intrusion into personal decisions, then has the Republic all but ceased to exist? If so, then is armed rebellion today justified? God willing, this oppression will be lifted and America free again before the first shot is fired."  — Former Michigan GOP Spokesman Asks If ‘Armed Rebellion’ Needed Over Supreme Court Ruling

"This government takeover of health care remains as destructive, unsustainable, and unconstitutional as it was the day it was passed, unread, by a since-fired congressional majority. Now as then, our first step toward real health care reform and economic renewal remains Obamacare’s full repeal, down to the last letter and punctuation mark. I urge every governor to stop implementing the health care exchanges that would help implement the harmful effects of this misguided law. Americans have loudly rejected this federal takeover of health care, and governors should join with the people and reject its implementation."  — Sen. Jim DeMint calling for unconstitutional nullification by states

But I save the most precious comment for last…​


I know what you did last summer

Yeah, I did this…​

…and this, and this, and this…

2 Notes

We did it.

Thank you for joining me and donating $40 for pediatric cancers research at Memorial Sloan-Kettering Cancer Center!​

Fundraising Goal: $4,000.00
Total Number of Gifts: 51
Total Value of Gifts: $4,794.40

It’s not too late to participate.


Help Me Turn 40 and Fight Cancer

​My 40th birthday is next week and I’m thinking about cancer. I guess it’s not a surprise that it’s upsetting me, but didn’t expect it to be on my mind so much. I’m thinking about my cousins Harry and Suri and Shirley, of friends have lost siblings and parents, of people I love who are still fighting. I thought my anger and grief had mellowed. Nope. They’re just routinely pushed aside.

I’m turning 40.  I don’t need anything. I’m sick of stuff. I have a wife that loves me and kids that can’t wait to hug me when I get home.

"A man once asked the Buddha to grant his family a blessing. The Buddha thought for a moment, then replied, ‘Grandfather dies, father dies, son dies.’ The man was horrified, but the Buddha shrugged his shoulders. ‘What other way would you have it?’"  — Buddhist parable

No, I don’t need anything for my birthday. But I want something. I want you to help me give a child suffering from cancer a better chance of reaching their 40th birthday. I want you to help me fund critical research in pediatric cancers, so that tomorrow children and their parents will no longer suffer.

Please forget the gifts and cards and well wishes. Just join me and donate $40 to Memorial Sloan-Kettering Cancer Center to fund their research into curing pediatric cancers. 

Thank you.


Can you guess who won this game?



Shots on target​



Fouls committed​

Yellow cards​

Ball possession​

Team 1​








Team 2​








Unbelievable will to lose.