The yin and yang of the engineering team and the sales team

There is a balance between developers and sales people that allows them to get along. This is sometimes the result of one team pushing the other to its limits, often the sales team pushing the limits of the engineering system already in place.  Its a dance that happens within startups everday.yin and yang

Through planning, brainstorming, innovation, and sales – these groups have  to work together in companies to get things done.

The power of the ignorance on the business/sales team side provides a childlike imagination that creates scenarios nobody has thought of, are not relavent, are overly complicated, and my personal favorite “computationally expensive” on the product.  Engineering can have the same imagination, but it is usually tied to the work necessary to complete the task and operates within the realm of possibility of the app. Vetting the technical feasibility ideas is the job of a strong engineering team keeps things in check.  They are always making room for innovation, growth, scaling, and constant  looking at security concerns.

The balance comes from the “asks” from each group that are constantly in flux.

On the one hand, the business team assumes anything is possible. Although technically this is true, engineering teams think in binary terms and all requests have a cost to other projects and future support.

Product planning is never easy, and prioritization is even harder. When you work on a web/mobile application either of those can change at a moments notice and a team has to be able to pivot in another direction at a thousand miles per hour.

Turn to fast and things get out of control. Turn too slowly, and you miss the mark completely.

I believe both teams need each other to stay in check. The ignorance of the business team to dream big, and the reality of the engineering team to keep things on the ground – and vice versa. It is not always the same balance, but the constant struggle between both groups is what breeds amazing products.

I have learned that these skill sets that can only be learned in a live environment which results in a win for users, customers, and the Internet at large as a result of this never ending storm.

To build a network, first help a network

I was talking to a friend a couple of weeks ago who wanted to break into and meet people within a specific vertical of startup tech companies. His approach was to feign interest in their offering and take a pitch from a salesperson. The thinking being that although there was zero chance of him becoming a customer, he could get time with a rep, learn about the offering and “build a network”.  I told him this wasn’t a good use of his time, and certainly not a good use of their time. The founding premise of the interaction would tarnish the reason for getting together in the first place.networking

I then shared a lesson my mother taught me about friendship which is; “to have friends, you have to first be a friend”. My professional version of this is the title of this blog post; to build a network, you have to help a network. You see it’s less about getting on a persons calendar for coffee or a meeting and more about finding out what you can do to help them.

A lot of people reach out for “informational interviews” or to “pick your brain” on stuff and the value exchange is lopsided from the start.  I hear of many of my friends/colleagues/CEO’s who simply decline by not answering.  This doesn’t help either side as the people writing the emails just figure they have to send more, be more persistent, or add more people to the top of their funnel.  This is a mistake, and instead they should think about the what I call the coffee equation which is putting in more time/energy into the ask before asking for something in return. You should give more first if you ask someone to have coffee so they know the agenda and feel good about spending the time.

Going back to the macro point, many people want to build a strong network.  To do this first by helping others you will not only understand their pain and problems first, but be someone that the person doesn’t mind connecting with in the future – especially after knowing you understand their world view and potentially help solve some of their problems.

To build your network, first help a network.

The State of US Tech Funding

The folks at Andreesen Horowitz and Benedict Evans put together this great presentation on The State of US Tech Funding.  It is embedded below and a lot of it rings true for what I am seeing.


I also agree strongly with Slide 39, that more smaller rounds are happening
Smaller Rounds
With the companies I advise, I have seen more of them raising a higher quantity of rounds at the so called “seed” stage.  The synonyms and nomenclature behind these rounds are also changing.  What was before a seed round is now a friends and family round.  Some even call these activities genesys rounds, or pre-seed deals.  Whatever the language, they are happening more frequently at smaller amounts – to my knowledge.
I also agree that while creating and scaling a software business is getting cheaper, reaching a larger online market is a growing challenge.  There are more SaaS tools and mobile marketing programs to use to “make it easier” but these end up adding to the burn of these Companies.  I jokingly referred to this trend as a re-distribution of funding via expensed $20, $50, and $100+ monthly SaaS plans happening between each company (no, thats not really happening but it is on a very small scale).
Great presentation to dive into to get a nice comparison between now and then, and to form your own opinion.

Sales Machine: What is a roller coaster rep?


One of the best parts about my events series Building The Sales Machine are the great nuggets I learn from speakers.  The latest of which is the question of; “What is a roller coaster rep?” as told by Bryan Rutcofsky of Yext.

Below is my discussion with Bryan which goes into details.

Basically a roller coaster rep is a person that appears on almost every sales team Bryan has ever seen.  Its a person that works really hard and does everything they are supposed to – which yields real results and new sales.  This then results in the rep reaping the rewards of this hard work and effort.  After that point, they are basking in the glow of success and are at the top of the leaderboards – but without investing in the work needed to stay there.  This process can be tracking by using KPIs – expectations from reps on a daily/weekly/monthly basis as a way to see if the effort is being generated.

Watch the video for the full effect, but I love this term and have been watching out for it ever since I learned about it.

Running apps for beginner runners

The state of running apps has certainly changed.  I went running Sunday for the first time in years, and wanted to see what the latest and greatest options were to geek out while running.  Three apps, 2.5 miles and 25% battery drain later I had a pretty good first run in awhile – both myself and with the apps.

I went with a combination of RunKeeper, Spotify (new running feature), and Nike+ Running.

It was actually very interesting to see the discrepancy between apps regarding time, speed, distance, GPS, and other features they all had.  Below is a maship of Nike + in app – the final result overlaid on the route I took in Central Park then a pic from the end that lets you put the trail taken on top of a picture.2015-06-07 15.57.09

Overall I would say I was pleasantly surprised from the progress of apps of 3-4 years ago (the last time I really used any). Many of my accounts were still dormant with my previous runs/workouts still in them.  Its amazing to think this data is just sitting there. Many have built in game mechanics now, reminiscent of the early Foursquare days, integrating milestones, badges, and social cues to stay motivated.2015-06-07 15.55.33

I would say that one of the cooler features I used was Spotify Running.  It seamlessly detects the tempo you are running at, and mixes the music to match.  Its a good motivator if you start to hear things slowing down, and a great “a ha” moment when you are going fast and the music picks up.  There was even a moment where the background sounds perfectly matched each of my steps and I thought it was the sounds of the trail I was on, but it was actually the music – great stuff.

Using multiple apps is certainly a battery drain, and switching between them while running is all but impossible.  I believe the results are worth the charge time and cumbersome nature of using multiples.  I also worry about data lock in and companies shuttering these services.  The good news is that most of the apps have integrations back into Apple Health and therefore there is a parent cloud record of what happens.  Of course the same could happen with Apple but I doubt it.

I didn’t activate any of the social posting features just yet, or join any “teams” or groups.  I think there is an aspect of putting yourself out there publicly to stay motivated and have been encourage you or comment on your runs.  I see friends doing this often and sharing they beat their latest distance/time/other and it seems to work.  I have a long way to go before this becomes a habit, but its a start.  Being near the park helps the most.  Until next time…

2015-06-07 15.23.50

5 Years at Foursquare

FoursquareI have spent the past year or so working on the latest advertising offering from Foursquare called Pinpoint. It’s really the culmination of my five years working Foursquare and an undertaking that was touched by almost every team within the Company.

In the months leading up to launch we have assembled an amazing team, some of the smartest people I have ever worked with. Interestingly they all pretty much had the same question before joining my team; “So why are you still at Foursquare?”. You see 5 years at a startup means something like 20 years at a regular company (or maybe that’s in dog years). I gave an answer that convinced them to not only join my team, and Foursquare, but also gave them confidence in their choice and I wanted to share those thoughts here.

As I approached this milestone, I really couldn’t believe it’d been 5 years. That’s the longest I’ve ever worked at any company, and feels like an eternity in start-up years. I have made some of my best friends at this company, and certainly worked with some of the smartest people ever assembled. I am sure I sound biased with these superlatives, but after interviewing countless candidates, and helping other startups recruit top talent, I can honestly say the caliber of people at Foursquare are unmatched.

“So, why are you still at Foursquare?” The answer is simple; I’ve had the opportunity to wear so many different hats within this Company that I might as well have worked at 3 different companies…or hat stores.

Its a longer story, but here’s the abridged version;

Chapter 1: The consumer story

Foursquare began its journey in 2009, with its flagship app connecting people to places and introducing a series of game mechanics that got people hooked. I had the opportunity to meet the founders (Dennis Crowley and Naveen Salvadurai) while working at Union Square Ventures and really loved what they were working on. The firm shortly thereafter invested in the Company, leading its first round. I helped with a few key projects for Dennis early on including changing the name from to, and soon took on small tasks within the company. Through what felt like a very organic process I gravitated towards some big tasks they needed help with. Shortly after, I joined in April 2010 as the first full time BD hire. Throughout this time I was on the other end of all the inbound requests and deals on the business development team and learned a ton. I could not have been happier, but always kept wanting to focus on monetization – not an easy task for a consumer facing company.

Chapter 2: Building the Sales Machine

After 2 years and a renewed focus, Foursquare doubled-down on its promise to connect places and people – and building a scalable sales infrastructure. While we made significant revenues in the past, everyone agreed that focussing on scalable revenue was key, and building a real revenue and sales machine. I next became the first person on the sales team, jumping ship from a very PR/spotlight heavy BD team. I got asked question ALL the time about the switch and why I left that group. Challenging myself in a new role to built up a team from scratch was my answer – I got a chance to introduce a sales infrastructure to a traditionally product, design, and engineering focussed company.

Job #1 was to find and hire my boss, our CRO (Steven Rosenblatt), which is an interesting task to say the least. We spent the first few months developing our relationships with existing “customers” (merchants) and asking them to give feedback on what would become the first ad products at Foursquare. Focussing on merchants first made the most sense and we soon introduced our first advertising product at scale, Promoted Places – paid advertising for merchants. This was followed of course by our second advertising product for brands (no physical locations) called Place Based Ads.

I helped build out a National Sales team in the US, focusing on clients and agencies at scale. We fast followed this with rolling out those same products to local SMBs and then mid market (think places with greater than 50 locations). Then I focussed on International sales in our biggest markets. I worked on bringing the same ad products to Europe and Latin America.

Scaling a sales team in this manner and adding this type of culture to a company is one of the hardest tasks I have ever had to do. There is a clear divide between those who joined the “consumer” company and those who joined the “commercial” company – and with those changes, people tend to either shape up or ship out.

Chapter 3: Building The Foursquare Audience Network and Pinpoint

After having two products in market for awhile, we soon realized that we were limited to focussing only on our own properties (app + web) and were limited to our own audience and scale. One of the next hats I wore at Foursquare was developing our out of app and off web ad products, which focussed in the programmatic space using a lot of the maturing mobile ad technology that has developed. This was a well paved road for advertisers who are using to placing traditional banners on desktop, mobile, video and social channels. This product, called Foursquare Audience Network (FAN), was a great addition to our sales arsenal. Giving us reach and scale, this was a great way to onboard our audiences into great platforms, only reachable by the Foursquare sales team.

The opportunity to go beyond the Foursquare & Swarm audiences became the next obvious step. Many advertisers were asking for more scale based on great performance to date. While we polished our in house programmatic practice, we embarked on an ambitious plan. The question was; “how could we leverage 6 years of location information and make sense of all the disparate signals out there.” The answer is Pinpoint. We looked at other apps, mobile ad exchanges, other third parties – partnering and creating a way to make audience segments for advertisers. Using 60 million places, billions of visits to these locations, and the best location signal parsing available, we are able to create audiences and bring them into the platforms we use like nobody else can.

This now marks my next chapter at Foursquare. Wearing many hats and having many roles has been the reason I have been here 5+ years. It has been an incredible learning opportunity for me building these things from scratch and watching the revenue story grow.

Building the sales machine within Foursquare has been a great experience and I am looking forward to what happens next.

If you are interested in joining the team visit our Foursquare jobs area.

Building the Sales Machine: Milind Mehere Co-Founder of Yodle

We are having our next Building the Sales Machine event next month with Milind Mehere Co-Founder of Yodle.  We are excited to learn from one of the best sales operators in NYC about building the organization.

Screenshot 2015-02-18 11.25.49

We are also excited to announce to launch a home on the web for Building the Sales Machine – a place for our event details, job listings, and videos of the events.

A special thanks to Dave Greenberger and Evan Bartlett who host the event with me and are now putting content into our new site.

If you are interested in attending a great event for those people building sales machines in NY (or anywhere!) please come out as it would be great to meet you there.

Building the Sales Machine Event: Bryan Rutcofsky from Yext

We recently hosted another Building the Sales Machine event at Foursquare HQ and it was great to see so many people working on building sales and revenue from NYC and other great places.

A big thanks to Bryan Rutcofsky from Yext for coming out for a great Q&A session about the early days, and getting tactical for the audience about how to build and retain a sales team.

We covered a broad range of topics including;

Validating a sales model
Going from 1 salesperson to 2 and scaling up
When the right time to outsource a sales team
Where to spend time
Deciding who to sell to
What sets top performers apart

Any many more!

We are trying something new this time and editing the videos breaking apart each question into its own piece of content.  Taking the nod from Gary Vaynerchuk we are putting out a TON of short form videos from the events with each question and answer being the content.  Instead of having to sit through the entire thing we can go deeper on each question and share short form Q&A (usually a minute or so) which is better for everyone.

Starting with; How do you determine KPIs set milestones for your sales team?

Here is another one about how to develop a comp. plan for sellers

Here is the full playlist

As always this is an experiment and we hope to learn a lot from this strategy and feedback is most welcomed!

Big thanks to Dave Greenberger and Evan Bartlett for their help


The startup accelerator application process

One piece of advice I have found helpful to new founders is going through the application process for startup programs.  Whether an accelerator, incubator, launch, or other flavor of program helpful to early stage startups – almost all of the application processes are incredibly helpful.  The goal of course is to have ready and willing founders ready to join the program, but not everyone should.  I will leave the why vs. why not to another post, but the application process itself can help founders get on the same page and outline the vision for their company.

The obvious programs that are top of mind for me are; YCombinator ApplicationTechStars Application500 Startups Accelerator Program, there are hundreds that have similar application questions

Questions this from YCombinator:

Ycombinator questions

Some questions I am paraphrasing that I ask during my mentor sessions that I find are helpful to founders

Who is on the management team right now?

How long have you been focussing on revenue?

What happens if you do not get into this program?

Who own the company and the breakdown of the ownership right now?

What are some of the challenges you have faced that are still unresolved?

What is the headline for your product launch in consumer/trade/enterprise?

…and the list continues.

These things make people think about things in a way that is structured and organized, and forces founders to come together.

Sometimes its easy to brush aside the more mundane and boring questions that really help define the vision for a business.  The application plays the “bad cop” in this scenario and lets the team focus on what is most important which is coming together and making sure they are on the same page for the future of their business.