Look For Opportunities To Accelerate

When you look at successful companies and entrepreneurs, what do you see in common? Is it that they were in the right place and the right time? Was it that they were harder working than their competition or peers? Or was it purely luck that played a role in their success? Depending on who it was, it could be one or the combination of all of these--but there's one thing that is common across all successful companies and entrepreneurs - acceleration.

I first became more aware of acceleration when playing competitive tennis growing up. When playing, you realize there's a point in a match when you started feeling like you could overtake your opponent. There may be a couple missed shots by him, a couple winners by you, and then you would start to feel the tide turn. When it does, you don't let off the gas petal--you accelerate. You accelerate by hitting more winners, forcing more unforced errors by your opponent, and you string together enough momentum so that you separate yourself enough that even at steady state, your opponent can't comeback. Opportunities for acceleration are almost difficult to describe, but it's something more derived from the gut. But when you feel it, it's crucial that you capitalize on it.

Another great example of acceleration was when I first started selling at Box. About 6 months into my sales role, I started feeling this inner confidence that I never had before. I felt like I knew how to qualify well, understood the messaging and benefits of our product, and felt comfortable developing rapport with customers. When all of this was clicking, I started to accelerate. In our early days, we used to have a phone system for leads that rang to everyone's desk, and the first person who picked it up would be able to sell to that customer. Feeling momentum on my side, I came in earlier and left later. I sat at my desk during lunch breaks. I literally placed my phone next to my keyboard so that I could pick it up faster with my left hand. I took every opportunity I had to get on the phone with customers. I accelerated as fast as I could, and it left me as a top ranked sales rep for the year.

If you look at three of our recent entrepreneurial success stories--Evan Williams, Andrew Mason, and Kevin Systrom--they each accelerated to build billion dollar businesses. What's common across all three of these founders is that they all had unsuccessful ventures first, then created new opportunities to accelerate into hyper growth . Evan Williams branched from the fledgling Odeo to found Twitter, then leveraged South by Southwest in 2007 to accelerate into the main stream. Andrew Mason transformed his first site, the Point, to Groupon, and accelerated to a $1B valuation in just 16 months through a hustling sales force and non-stop media attention. Kevin Systrom pivoted from an unsuccessful check-in service called Burbn to Instagram, garnering 50 million mobile users in under 2 years through social acceleration, network effects, and top-notch usability. None of these founders sat idle when they started to see their numbers tick upwards. They each threw a ton of time, effort, and venture capital into accelerating their growth.

To grow as a successful product manager, it's important to always be on the lookout for acceleration opportunities. If you feel like your team is really hitting its stride, don't let them settle for the status quo--push them to get even more done. If you start seeing trends in user acquisition, invest even more into those channels. If customers start loving a specific new feature, don't hesitate to dig deeper and draw even more attention to it. Acceleration opportunities don't usually wait around, so when you see them, make sure you seize them.

How to Give A Killer Product Demo

If you’re in product at a small startup, it’s highly likely that you’ll be owning product while also selling it at the same time. Sales is a skill you need to master because it can literally determine the fate of your startup.  In most scenarios, I’ve learned that if you build a product, they will not always come.This is where you need strong selling skills.

I was lucky to join Box in the beginning of 2011 in a selling capacity. I sold SaaS for two years primarily over the phone, with the occasional visits to large clients. I estimated that I gave around 350 demos during that span and during my peak months during our hyper growth stage, I was closing 30 to 35 deals with businesses. The secret to my success was delivering an awesome web demo, which is the crux of most SaaS startup sales.

The Web Demo

First impressions in SaaS are extremely important. If you think about it closely, the web demo is like taking a test drive of a car when you’re at the dealership.  You may have done your preliminary research online or through word of mouth, but getting hands on with the car could be the make or break.   For example, when I bought my last car, I was dead set on a Mini after weeks of research and seeing it around the roads in SF, but the moment I stepped into the car, I knew it wasn’t for me.  Similarly, it’s crucial to deliver a solid web demonstration to prospects to make sure the sales cycle gets off on the right foot. 

Preparation
Make sure you block out 30 mins to an hour before your demo to prep for your demo.  If the client looks more promising, block out the full hour to be safe.  Do a quick skim of their corporate website, financials, LinkedIn profiles, and a basic Google search of the prospect your pitching to in case there are things you should know about them (like an award they won, an article they were mentioned in, etc.).  Once you understand who you’re selling to, then create a basic outline of how you envision the demo going.  I started with the one main thing I wanted to accomplish in the meeting, then built an outline from there.  For example, if I wanted my client to launch into a 30 day trial after my demo, I would tailor my demo flow around convincing him that a trial is the way to go.  

Demo flow
Most my demos lasted an hour and flow like this: 15 mins qualifying the customer, 30 mins demo, and 15 mins discussing feedback and next steps.  In terms of importance, the qualifying portion is the most important part of the demo, with the follow up being second and the demo the third.  During the qualification period, it’s important to have 3 or 4 key open-ended questions ready for the client.  I typically lead with questions like “why are you interested in a solution like Box and what business need are you trying to solve”?  From there, I let my prospect’s answers guide me to how I should tailor the demo.  For example, if the client says they need a way to enable their sales people with the latest marketing materials while on the road, I would tailor my demo as if I were a sales person in the field who needs to find data sheets for my customer while using my iPad.  In the feedback and next steps phase, it’s crucial to close on the client for some type of commitment.  A “close” rarely means to get them to buy the solution on the spot, but rather, to get commitment to move along the sales cycle.   A great example of a commitment from a prospect looking at Box is for the client to get their technical team on a follow up call to do a deep dive into security and administration aspects of the product.  If they agree to it, try to nail down th exact day and time you’d like to meet and send them an invite immediately after the demo.

Follow up
Follow up separates the good sales people from the best.  The top sales person last year was always master of follow up.  She’d take all the top discussion points from a demo and list them along with the proposed next steps in a clearly written email to all attendees.  I usually started my follow up emails with the business driver of why they may need a solution like ours, then bullet out the follow up items.  Then, when you want to get an update from the client of where they’re at in the sales cycle, you can always refer or reply back to this email.

Bonus points
I also picked up a few pointers from other colleagues that have made my demos run even smoother.  First, try to stand up as much as possible.  This helps your voice project and pacing will always help calm the nerves when speaking with new clients.  Second, if you’re on a group demo, try to turn on your webcam at least the beginning, if not all of the demo.  This helps put a face to the name and is a great substitute for not being there in person.  Last, try to have dual monitors set up during your web demo.  Use your non-screen sharing screen to do behind the scenes research, take notes, or prepare a piece of the demo before presenting it to the clients viewable screen.
These tips will not guarantee sales or turn you into a demo king, but I’m a strong believer that sales is most successful if you put science behind the art. If you have a successful formula that you continue to iterate on, you’ll do better statistically over time then other sales reps who don’t approach their sales cycle systematically.

Sprint Retrospectives: Small Changes Can Pay Huge Dividends

My favorite part of the sprint is the retrospective.   It gives you the chance to step back, reflect on your work and progress, and set up new goals for the future.   Our team has an awesome tradition of holding our retrospectives at a local bar down the street.  We order a couple beers, lay out a few markers and stickies, and openly discuss how our sprint went:

The reason I enjoy our retrospectives so much is because of how honest we are about ourselves.  If someone did a good job that went unnoticed during the sprint, we are quick to give praise.  If there’s something bothering us, we don’t hesitate to voice our opinions and discuss the issue.  Everyone has a voice during our retrospective and we literally discuss every single sticky that is posted.

What’s great about this transparency are the changes you can make.   Take a recent sprint that we just completed—during our retrospective, we admitted that we were spreading ourselves too thin with not enough focus.  We were doing multiple stories at the same time, allowing story scopes to get out of hand, and also putting in too much work on un-related projects. We were working, but not working smart.

We discussed this very candidly during our retrospective and were all in agreement.  We decided to make a small change: during our next sprint, we would have one goal—work on getting our new service to production.  With every story, we asked ourselves, will this help us get the service into production?  If not, let’s not load it or work on it.  Since we hold our retrospectives right before planning, this gave us a clear mission when we were dragging stories over from our backlog to the next sprint.  When we came back to work the next Monday, we clearly understood what we wanted to get accomplished over the next two weeks.

The focus paid dividends. With one small change, we were able to take our average velocity per developer from 14.33 to 22, a 54% improvement!  When reflecting on our progress after the  sprint, we all agreed that the focus helped us knock down a ton more stories and get into a very healthy rhythm of development.  

It’s important to always remember that every sprint has room for improvement, so don’t hesitate to make changes and try new things.