A Tough Week

On a personal and professional level, this was one of my toughest weeks since the company was launched in the autumn of 2005. It was made especially hard because this week saw the departure of an employee who’s been with us since the start. It was awful in many ways and I found myself physically affected by it to the point of nausea, loss of appetite, sleeplessness, and when I could sleep, I had nightmares. It was truly a shitty week.

Additionally, I had to pitch the board on something and it didn’t go over with showers of rose pedals and applause. C’est la vie – I get my 2nd swing at it in a couple of days.

On a broader level, not just isolated to this week, we’ve had a hard time finding qualified sales people and in a couple instances made offers to people who just decided to not show up on their first day. Nice huh? It seems, though, that the dust has settled now. We’ve a couple new people who started with us this week and they appear to be taking well to their jobs and to the company culture – two things I watch very closely in those first few days.

Yet, Tuesday we had our monthly company lunch and morale is good and healthy! At lunch we went around the table and told stories about our most embarrassing work moments, or most demeaning jobs. There were some good stories told!

We’ve got a marketing intern starting with us on Monday and I’m actively interviewing to fill the newly opened role. We’ve got two more sales people scheduled to start over the next few weeks.

Anyway, the point of all this is that my job, for the past couple of years at CitySquares, has been entirely about building a business and a company, and it still is. We’re in ‘build’ mode, there’s no two ways about it. I enjoy that work greatly. Now that our staff is in the double digits my job is becoming increasingly more about managing the organization. I also enjoy that work greatly. I think I’m good at both of these things, which is why, ultimately, I enjoy being an entrepreneur and CEO. My previous company saw about 12 full time staff at it’s peak, but dozens of contractors around the country, nearly all who reported directly to me. I also was the direct contact for most of our customers. I greatly enjoyed that work, the hustle of it all. It makes me wonder too though, about those entrepreneurs that aren’t able to make the transition from founder/builder to manager/CEO.

So back around to tie it all off – it was a tough week, the worst yet. Unfortunately, as a manager, tough decisions need to be made. Unfortunately as a CEO sometimes you gotta take a few jabs from your board. But at the end of the day, this is a business, that’s the bottom line. And at the end of the day I need to be able to look at the books, look at my board, and look at my staff confidently – knowing that I’ve done the best job they expect from me. I have to be accountable. It’s not easy, I didn’t sign up for easy. And I also need to be able to look at my own reflection and know that I’ve done the best job I expect of me. And the two are not separate – they are the same.

So to wrap it all up I thought I’d share a funny video that someone sent me on Monday – the timing was great. This person had no idea that I was entering a shitty week either, just really good timing on their part.

Update (long overdue)

Last weekend I was fighting a nasty cold and decided I’d post an update up here. After typing and editing for what seemed like an hour, I accidentally hit the Backspace key and found myself going backwards in my browser, and when I clicked forward, my blog post was gone. I was pretty pissed off. So, I’m feeling better this weekend, less fat-fingered, and I’m going to take another shot. Here goes it. By the way, this is long, but as always, in the spirit of transparency and honesty, I’m going to give you all I can.

(Quick side note: Be my buddy on Citysquares.com! You need an account.)

Update on company morale: It was very interesting. About 4 weeks ago I started to pick up on a vibe of discontent among our small staff. I honed in on it for a couple weeks, listened closely and found it was true. I think it started right after the launch of the new site. The staff was really hyped up about the new launch, but it got delayed by a week. That was the first disappointment. As a result of all the enthusiasm around the launch, the staff was also hyping customers and partners. The launch went a week later and it went well, but as usual, not without bugs. And for all of the Citysquares staff, except for me and Bob, this is their first startup experience, certainly their first web startup. So they felt a little disappointed I think, because of the delay and the bugs, and because the fizz in the bottle didn’t add up to the big explosion everyone was expecting. I realized that I had to become more engaged with everyone and address these matters one by one. I was stuck in my office, helping Bob and Justin fight fires on the site. I needed to stop that, and get out in front of the team and put their minds at ease and share the plan. After opening the lines of communication, top to bottom, side to side, and working with Bob and Justin, first, to set the plan, and then once it was communicated across the company and other channels, the stress went away and everyone started to breath easier.

On top of all this, as the company continues to grow, new personalities enter the equation and new relationship dynamics sprout and change. I suddenly had flashbacks of days at prior startups, and how it’s so important to water the seeds of those relationships and keep the soil fertile, and also to clip off the thorns. When you cut right down to it, the company is only as good as our people. And people, well, need people. We spend more time with each other than we do our own families, for the most part. So it’s critical to build this company from the ground up with deep rooted relationships firmly in place – that starts now. I firmly believe that those relationships, those bonds, can be the source of greatness for the business, or the source of something devastating. Anyway, morale has gone from OK to great, and mostly because the stress of the launch is gone and also, we’re doing more together, as a company. For instance:

  1. Beer Fridays.
    Every day at 4pm, we have a beer and wind down the week, we joke around, we chat, and relax the shoulders and posture – just chill. Last week we had our first, and while most people actually stayed at their desks, the vibe was very loose. People were joking around, instant messaging each other, and friends, busting each others chops a little and letting off a little steam. Last night, we all went next door to Gaslight for a drink. It was good – lots of laughs, and more letting off steam.
  2. Monthly company lunch.
    Once a month, on a set day/time, we all either head out to lunch together in town, preferably nearby, or we order in. The purpose of this is the same as beer Fridays – don’t take things so seriously, get out from behind the desk, stretch the legs, relax the shoulders, have a little fun, and build bonds. But also, to talk about company matters, changes to any policies perhaps (yes, this web startup does have policies), and to just open up the lines of communication. This is very important. This month we went to JJ Foleys Cafe and it was a good time. After lunch, the office was in 5th gear – I was very happy to see that. This is going to last until the company gets so big that it just gets too expensive and we’ll have to slim it down a bit. But for now, it’s totally manageable.
  3. Holiday outing
    So we were all thinking that we could have a big Citysquares.com holiday party. Maybe we’d invite customers, users, friends, partners, etc. But the more I thought about this the less practical it became. Just too much, right now. Maybe sometime next year when there’s a better reason. So we opted instead for a company outing. We’re still trying to figure out where, but we’re thinking of going to F1 Boston, or to a paint ball range or something, and then a big lunch in the north end. Not quite sure, but this is the direction. We’ll do it on a Friday, perhaps December 14th. We’ll shut down the office, leave at like 1 or 2pm, and go have some fun. This way, a) it doesn’t impede on people’s personal time and b) it’s a free half-day off.

Well, that’s a big one. It’s pretty detailed but I thought it was a good entrepreneurial topic that you might enjoy.

Update on the new site launch. The site launch went well, albeit late. And like any product launch, it didn’t go off without a hitch – it had it’s fair share of bugs. The feedback from folks was quite immediate and ranged from raves about the new design/look/feel, compliments and sometimes confusion about the new navigation, to complaints about certain functionalities and features. Things that people loved included: design, navigation, breadth of the site, fusion of some new social features with local search. Things that people didn’t like: search, navigation, user profiling (People Profiles). Bob and Justin were quick to fix some navigational issues, and that continues to be a work in progress, and they also quickly fixed some of the people profile problems that we launched with. Search continues to be the biggest problem, and the new search functionality is on track to be implemented at the end of November. That’s probably the biggest thorn in our side right now, as it pertains the site experience. Bob and Justin are also working hard to revamp some of the customer profile pages and upgrade some UI stuff, specifically on the city/neighborhood home pages. Too much real estate is being used by the map and the businesses are far too low. This is going to be fixed next week I believe. As always, these things are to be expected and improvements are going to become more frequent and rapid. Bob and Justin have some very exciting plans for the site, once these bugs and fires are take care of. All things considered, the new site has impressed many and is a huge upgrade from the old site and we’re very pleased.

Sales. As I’ll tell you over and over again, Citysquares is not a technology company – we’re a sales and marketing company. That’s where we invest most of our dollars. Our goal is revenue, not widgets or Facebook apps (at least not yet…). Much of my job is to oversee these efforts, and so far Citysquares is doing a hell of a job with sales. Last month we had another record month. I am becoming more and more impressed with a) our sales manager Phillip, and b) our two full time sales people Kim and Jason. The three of them work extremely well together and when they get into 5th gear, boy are they good.

We had a strange incident with the sales team this week actually. We hired a new guy who started on Monday. He quit on Friday for “another offer.” Phillip was pretty ticked off and just had him leave right away, and I would have done the same thing. Everyone took it very lightly and even laughed it off, but we have to be more careful and listen to our guts a little more. I think most, if not all, of us had a feeling about this guy. It’s caused us a bit of frustration because now we have to fill his seat and that takes time and money. It’s OK to laugh about this once, but we need to be sure this is the last time.

Other things. There are lots of other things I could talk about in great detail, but this post is going on long enough. I’ll run through a few things though, briefly:

  1. HR – Yeah, yeah, we’re only 10 people, but ya know, it wont be long until we’re 20 and handling HR matters is going to become a real pain the ass. We offer competitive salaries for everyone, stock options for most staff, and a great Harvard Pilgrim Health Care HMO plan. But two of the employees’ families are growing, we’re hiring more people and their needs are different, and we need to be able to a) offer more benefits and do so cost effectively, and b) offload some of this management. We talked with AdminiStaff. Frankly, I was not impressed. They couldn’t give me a straight answer as to how much their services would cost me, per employee. Isn’t that the bottom line??? Not for them I guess. We are talking with TriNet – much much better! We’re running some numbers and we hope to be able to use them starting Jan ’08.
  2. Marketing – going well. We decided to have less control over the tactical approach to the marketing, we accepted the fact that we don’t have a resident marketing expert and we should really let our partners have more control over the approach, and get a little less hands-on. We should help establish the strategy, the goal, the vision, help build and approve the plan, but then let our expert partners run with it. This is why we have these partners. We decided on this about 3 weeks ago, and it seems to be working well.
  3. Traffic – growing nicely. Alexa sucks. Quantcast is pretty cool. Google Analytics is rockin. I trust AWStats the most though. Uniques are growing nicely, repeats are steady, page-views are already at an all time record high this month. I want to see much more though. We’re working to tweak our SEO, and improve upon our content strategy, and marketing is a big part of this, so are partnerships with content and media partners. Speaking of which…
  4. I hope to announce a new and exciting content/media partnership in the next couple of weeks.
  5. Hired an office manager, Amber, a couple weeks ago. So far that’s working out very nicely! I can actually get back to working ON the business, not so much IN the business.

Well, that oughtta do it. Wow, this was a long post. I guess that’s what happens when you let it go so long. Sorry for the silence everyone!

Looking for kickass Office Manager

Citysquares.com, a growing Internet company in Boston’s South End is seeking an experienced, youthful, energetic administrative professional to support the company in day-to-day operations, managing the administration of the office, as well as representing the company in a professional manner. This position involves interacting with management, personnel, customers, vendors, and partners. High spirits, smiles, positivity, and a cool-head are as important as experience and skills.

Principal Responsibilities

The work will be varied, but will include:

• Organizing mail, filing, records, and billing
• Handling day to day Accounts Receivable and Accounts Payable with QuickBooks
• Supporting the CEO scheduling meetings, booking travel, answering phone and email, and assisting with projects as needed
• Assisting sales and customer support team
• Preparing reports and presentations
• Assisting customers and fulfilling customer orders
• Other duties based on skills and experience

Experience and Requirements

• Enthusiastic, personable, pleasant
• Demonstrating a high degree of professionalism in speech, manner, and appearance, with confident personality and poise and assertiveness as needed
• Self-motivated, team player with no attitude
• Demonstrated success in prior work
• Ability to stay organized and keep others that way, detail oriented
• Capable of communicating and working effectively with senior management and executives at key business partners or customers
• Knowledge and comfort with the Internet and a high degree of skill with Microsoft Office (Word, Excel, PowerPoint, Outlook) and QuickBooks
• Experience in a start-up, financial or internet company a big plus.

The company offers a fun and exciting work-environment and an opportunity to participate and grow in a small, fast growing company. Compensation based on experience. The position is full-time.

Minimum requirements
The ideal candidate has 2-3 years of administrative or related experience, and the capacity to work within a start-up environment. Advanced knowledge of Microsoft Word, PowerPoint, Excel, Outlook, QuickBooks required. Must possess excellent organization skills and have a high attention to detail with a desire to get the job completed accurately and in a timely manner. Must be self-motivated, have excellent interpersonal skills and the ability to build professional relationships. Ability to work independently and as an effective and engaged team member in a fast-paced environment and must be able to keep cool during high stress situations and deadlines. Strong initiative and follow through is essential.

IMPORTANT: Kindly send your resume, a cover letter, and your salary requirements. If you do not do provide that information, you will not be considered.

If you, or someone you know, is interested just email me at bsaren -at- citysquares.com.

A Good Month, a Good Quarter

Being that it’s June 29th, the last business day of the month, and the last business day of the 2007 Q2, I must take a moment to reflect on the excitement that I’ve felt today, and through the past 3 months.

Three months ago today, it was the last business day of March, also a Friday. Looking at my Outlook calendar I had one meeting scheduled – a telephone demo with Iotum (Talk-Now). Ali’s graduation party was the next day. The deal with eCoast hadn’t closed yet, but it was imminent and the announcements were all but formal. We were still working out my basement, 2/3 of us were anyway. And we didn’t have any real solid prospects on a sales manager.

Well, I’ll spare you from the minutiae of the rest of the days thereafter, and most of the updates are here on this blog. In a nutshell though, our new Manager of Biz Dev, Phillip Dias, joined the team, and soon after he hired Zac Champa to work with him. Both of these guys are just rock stars, I’m very pleased with the quality work they do, the energy they bring, their attitudes and their cultural contributions.

Chris has some awesome community activities planned, some great campaigns incubating, and he continues to contribute to sales.

Bob is starting to heat things up with respects to product development, hiring an engineer, and getting a new site/platform built in time for the holidays (knock on wood).

We also have an office now and aside from some acoustical concerns, we’ve settled in and are quite happy. We’ve even made some new friends, like Mike Freedman and Paul McBride. We have some great new customers, some early partner oppty’s, and a big outlook with many challenges and many promises on the horizon.

Today was a big day, in more ways than one. We made our numbers for June, we had some breakthroughs, we formed a tighter bond with some customers, we also formed a tighter bond with each other. We had dinner and drinks at Redbones tonight too. Zac thanked everyone for making Citysquares the best job he’s had in a long time, Phillip, Bob and Chris shared their sentiments, as did I.

Today was a very good day, in more ways than one. And looking back to 90 days ago, we’ve really made some big progress.

Undoubtedly the good-times can’t last. That’s not how life works, that’s not how business works. There will be hard times and tough days, tough months, even tough quarters. July will not be a picnic. It will be a tough month and August will be harder. No picnics here at Citysquares.

But today, June 30, 2007, is a good day that we’re enjoying. These days make the others much more tolerable.

REVISED: Seeking Developer for Full Time Position

CitySquares is seeking a full time Drupal developer. Please see below for more details. If you know anyone, please send them my way. Thanks!

Internet Applications Developer


Citysquares is seeking a talented, skilled, and innovative Senior Web Applications Engineer to work primarily in PHP, MySQL, MVC platforms (e.g., CakePHP) as you improve our website’s infrastructure and work alongside a Front End Web Developer. You will create dynamic web pages based on the Drupal technology, possibly MVC source code and reusable classes that will not only improve our website’s general infrastructure but also increase effectiveness for customers and users. As you develop and implement new features and address mission-critical issues, your strong understanding of Object Oriented Programming, SQL skills, and a basic familiarity with Web 2.0 technologies (AJAX, Ruby) is important. You’ll play a critical role in our small, fun, and innovative Internet startup where creativity and excellence is recognized and appreciated daily. This position will rely heavily on your experience and judgment to plan and accomplish goals.

Candidate should have superior technical skills, excellent communication and cross-group skills, and a desire to work in a casual and fun environment where hard work is the norm. This position requires an ability to quickly master new technologies and applications, agile development efforts, and a passion for quick results.


• Improve the existing website infrastructure.
• Build consumer-facing web-based applications.
• Design, build, enhance, and optimize content management and dynamic new media platform, content distribution and syndication infrastructure
• Take ownership of end-to-end development efforts including requirements definition, data modeling, network and database infrastructure, website development, and more.
• You will be programming on Linux, utilizing primarily Drupal, and perhaps a mixture of Object Oriented Programming solutions, and MVC frameworks, Javascript, PHP, Perl, and Python.


• 4+ years as Web Applications engineer.
• 3+ years in database design and data modeling (MySQL focus preferred).
• Must be extremely proficient in PHP, Perl, MySQL, XML
• Big bonus points for experience with Ruby, other forms of MVC
• Network administration and programming in UNIX/Linux environments.
• Multi-level security database design.
• Strong interpersonal and team skills.
• Willingness to have fun, experiment and try new things
• Must be passionate about working in a high-energy, funded startup.

If you are interested, please send your resume to jobs-at-citysquares.com. Thanks!

We Need a Sys Admin

If you know a good Linux/Apache sys admin, preferably in the Boston area (but not an absolute requirement), please send them my way. We need a new sys admin. We’re looking for a freelancer/contractor who understands systems administration, the importance of uptime, and just how important it is to be proactive and take initiative.

Please send them my way!

Thanks so much. Here’s a link to the job on CL.

A Taste of Progress

Well I have to admit that today was probably the first really great day here at CitySquares. Today just felt like progress was in the air. From early in the morning through this hour things were just happening, all day. Phillip and Zac were just kicking ass today and they took June sales from good to great. Bob is really cooking on the IA for the new platform, the comps, and readying for his presentation the BOD on Monday. Chris is really starting to get the marketing and PR stuff moving and some really great ideas are in the oven. Our advisors are coming in tomorrow for a meeting and to discuss lots of things.

One of the coolest things that’s starting to happen now is we’re starting to really perform as a team. The office is just abuzz. People moving around, phones are hot, faxes coming in and going out, ideas are being discusses, priorities are being targeted, fires are burning, and everyone is getting along really well. The energy and morale is very positive; lots of smiles, and there’s just as much dialogue and debating.

Today felt great all around. There will be highs and lows, but my gut is telling me that this is just a taste of what’s yet to come.

Priority #1: Sales

After about 4 weeks of interviewing candidates for our business development manager position we settled on our final candidate and made him an offer this weekend. Interestingly enough, as I had hoped, we found our new rainmaker by tapping resources – free ones. We didn’t find him through recruiting firms or from Craigslist. We knew what we were looking for in this person and we sought it out, very aggressively. I didn’t sit back and wait for the resumes to come in. It doesn’t work like that.

I’m sorry but I’m going to keep saying “he” and “him” until he officially starts; Ya just never know.

So he has all the characteristics we were looking for:

  1. Experience: Strong inside and outside sales experience. Bonus: Extremely good market experience.
  2. Guts: He’s willing to jump in and ready for the next step in his career. He wasn’t even on the market when I first contacted him. As my father always said, “the best jobs are the unadvertised ones.” True that.
  3. Drive: He really wants more. He’s got a hunger and a passion, for life and for success, and prosperity. He probably hasn’t quite harnessed those qualities yet because, professionally, he hasn’t had the opportunity. Now he does.
  4. Cultural fit: He’s about our age, he knows the space, he understands the Internet and how it fits into peoples’ lives, he totally gets the market too. Equally importantly is that I don’t see a reflection of ourselves when I look at him. It’s time to freshen things up a bit – bring in some new blood, with some different interests, different opinions. He’s going to fit in really well I think.

So for the past few hours I’ve been on my laptop doing a massive brain-dump of all the things I’ve ever envisioned for a CitySquares sales organization. I’ve documented everything from compensation and incentive plans, to processes and market data. It’s the new and improved CitySquares sales organization.

If it ain’t about sales – it’s a distraction. It’s a fire and it must burn. We’ve got a lot to do over the next few months, but sales is the top priority, and the second priority, and the third priority.

Citysquares is Hiring

Clearly if Citysquares is hiring, something is up right? Well, as much as I want to be 100% transparent and brutally honest, I have to hold back for just a little bit. Conclude what you will, but I will say no more for superstitious reasons, but also to respect the privacy and my relationship with others. I will stop there. More to come though. Please forgive me if I’m violating some hidden secret code of the blogosphere.

Citysquares is currently seeking candidates to fill the positions listed below. If you know of anyone who might be a good fit, please let us know! Any questions can be directed my way.

These jobs can also be found on our website at http://www.citysquares.com/about_jobs.html.
That’s all folks! Wink