When John Kelley took over as CEO of CoachUp in January 2015, he never imagined his previous experience marketing test prep options at The Princeton Review would be so relevant to selling the concept of private coaching.

“I always had to market to both kids and parents,” he said. “At CoachUp, it’s the same concept. The parents are typically paying, and they need to understand the value of private coaching.”

CoachUp is a Boston-based startup founded in 2011 that hires top level athletes to provide one-on-one training. The company offers an online marketplace that matches athletes with private coaches in a wide range of sports—from football and basketball, to yoga and running.

While Kelley may no longer be pitching the benefits of private tutoring versus an online course to prepare for the SAT, he is still focused on helping students succeed with the help of their parents.

Under Kelley’s leadership, CoachUp recently surpassed 250K training sessions on its platform, and is expected to onboard coach 20K later this month. The company has quickly expanded across the country, and currently offers 35 different sports to athletes of all ages.

I recently sat down with Kelley to talk about the new direction he’s taking CoachUp, how the company’s target customer has changed, and how he plans to attack a potential $30B market.

A NATURAL FIT

Kelley is a native of Cincinnati and a Harvard grad. He worked 13 years for larger corporations, including Procter & Gamble and Johnson & Johnson before catching the startup bug.

He returned to Massachusetts and was employee number 10 at Waltham-based Imagitas, a marketing services company that was eventually acquired by Pitney Bowes for $230M in 2005. He also led marketing at Monster.com, and was the CMO at The Princeton Review during the time it was acquired by internet giant IAC in 2014.

CoachUp founder Jordan Fliegel stepped aside from the company last December to work on a new venture and book release. Fliegel reached out to Kelley based on his experience in marketing and success scaling businesses and online marketplaces, which was critical as CoachUp looked to expand in 2015.

“My first focus was to understand the business,” Kelley said. “One of the key areas I focused on was optimizing and refining our brand to speak to who our customers really are. When I came on board, there was very much a male-centric, jock orientation to the brand. That’s not who our customer really is.”

AN EVOLVING BUSINESS

Kelley reads each and every one of the coach reviews clients submit after a session. He’s found that, although kids are the end users of CoachUp, parents are typically the ones making a purchase decision. The mom, in particular, is often the customer.

“We’ve found that this experience is not necessarily about the skills,” he said. “It’s about the confidence, self esteem, and the way a child responds to someone other than a parent or team coach who decides what their playing time is. It takes the parent back into being a parent, and lets the kid enjoy the sport and get better on their own terms.”

When Kelley joined CoachUp in 2015, the company was focused on the 12 to 18-year-old demographic for major team sports, like basketball, soccer, football, lacrosse, and baseball. These sports represented 90 percent of the business, he explained.

But more recently, CoachUp has been attracting athletes who are both younger and older than its original target customer.

“As the business has grown, we’ve seen more people getting involved in post-collegiate sports and activities—whether that’s strength and conditioning, yoga, pilates, golf, tennis, or even triathlons,” Kelley said. “And more parents want to get their younger kids involved in CoachUp. Many parents just want their kids to get involved and try different things.”

In August, CoachUp will be launching an event in Boston called “CoachUp Play”, designed to expose four to ten year old kids to a variety of sports in a group setting. Kelley explained the event is part of the company’s push to market to a younger audience.

THE COACHING EXPERIENCE

Tim West was playing basketball at a sports club in Los Angeles one day when Fliegel approached him and asked if he’d like to make some extra cash.

“It sounded great,” West said. “I really didn’t know what I was getting into, but people started reaching out to me right away.”

West has been a coach at CoachUp for the past five years. He’s originally from Chicago and received a scholarship to play basketball at Northeastern University before being drafted professionally into the Korean Basketball League. He is currently a physical education teacher in the Boston Public Schools system, and teaches basketball for CoachUp in his free time.

“The families are so grateful for this experience,” West said. “Parents really look up to you. They call you and tell you their kid is improving. It’s a great feeling. And I love the relationships I’m building through this.”

All CoachUp instructors must have coached at least at the high school level, or played in college or professionally to become a registered coach. For many coaches, their playing careers are over, so CoachUp is an opportunity for them to stay involved with the sport they love.

“This really just started as a way for me to make some extra money, but I’ve grown as a coach and found this experience to be incredibly rewarding,” West said. “I love helping these kids reach their goals and take their game to the next level.”

GOING AFTER THE LARGER POT

Looking to the future, Kelley and the CoachUp team want to create more value for coaches. This includes expanding the functionality of the CoachUp platform to give coaches more flexibility beyond one-on-one coaching—like sessions with four athletes, camps and clinics with 20 athletes, or multiple coaches could collaborate and offer a session for 500.

This fall, Kelley plans to give coaches the option to put some of their own content on the CoachUp platform, and conduct virtual sessions online.

“Coaches have egos and want to build their own brand,” he said. “They want a way to interact with other coaches and clients. With 20K of them, they’re not all great writers or videographers. But there is a solid core with good content, and we want to push that going forward.”

CoachUp has quickly expanded across the country, setting up major markets in California, Texas, Florida, New York, and Illinois. Kelley said the company has gotten smarter at optimizing the supply and demand of coaches and sport offerings in each market—having more than doubled its conversion rate over the past year.

“We’re the first to move into this category, and there’s no one that has taken the broader market approach that we have,” Kelley said. “There’s a $30B available market in U.S., and we’re operating at a very small sliver of that right now. We have the opportunity to go after the larger pot.”

Bennet Johnson is the Digital Marketing Intern for VentureFizz. Follow him on Twitter: @bennet_15

Globally recognized, Acquia offers the leading cloud platform for enhancing and optimizing digital experiences. The Acquia Platform brings personalized real-time customer engagement to life for the right person, at the right time, on the right device. Delivering world-class customer experience is the business they're in.

Their HQ is located in the Financial District in Boston's 13th tallest building: Exchange Place. The color-changing elevator lobby sets the mood for their vibrant space. Sleek and stylish are among other words that come to mind when entering the spacious lobby enhanced by high ceilings. The flow of the office opens up into the kitchen filled with various seating spaces to meet with your team or enjoy your lunch.

All work and no play? Not here. There's a game room showcasing a ping pong table, giant chalk board for doodling, and gaming systems for a solid mental break. Are quiet spaces more your thing? They've got you covered with a nap room, adorned with hanging pods and cushy, giant bean bags!

Customer experience isn't the only thing Acquia is good at, there's no doubt that they're enhancing their employee's experience as well! Enjoy the tour.

Acquia is hiring! Check out its BIZZpage

Like many women, I rushed to the theatre the other night with my girlfriends, eager to see the highly anticipated “Bad Moms.” While it wasn’t the next great Oscar contender, it resonated with all of us. Why? Because whether you’re a mom or not, it’s relatable.

The premise of the movie suggests none of us can be perfect. When we aren’t perfect, we are considered “bad” at what we do. Striving to do our best is different than attempting to achieve an unrealistic standard in our lives unilaterally. The trick is prioritization and confidence.

PRIORITIZATION

Whether you’re a mom, dad, pet owner, or just have a life outside the office, so many of our existences are filled with things we have to do, as well as the things we want to do. When you partner all of those things with a drive to give your very best at work, you’re looking at mental and physical burnout.  

The trick is to determine what truly matters to you. Give your best efforts to those things. Everything else needs to take a lower priority.

For example, I’m a single working mom. I quickly figured out that if I wanted to be home at night to make dinner for my daughters and spend some quality time catching up with them in the evening, I would need to hit the office at the crack of dawn so I could use that quiet block as a “get my work done” time.

It’s definitely not fun when the alarm goes off early and I’m at my desk by 6:30 a.m. But the prioritized time I get on the back end to achieve my mission of spending that time with my kids is invaluable.

I work with plenty of people who edit their schedules to prioritize what works for them. Some trade their lunch break for the gym because health is important to them. Some listen to podcasts during their commute so they can fuel their brains with new things. The point is we’re all individuals with different things that are important to each of us.

WHAT YOU CAN DO RIGHT NOW

Make a quick list with two columns. One side is the “must do,” and the other is “want to do.”  

List everything on both sides. Prioritize what’s most important to get done well. And then get creative. For example, cleaning my house is an important thing, but deciding to invest a little money to have someone give it a thorough cleaning became well worth it in terms of the time I got back to do things I valued doing more with my time.

I see other busy people ordering healthy lunches to the office in order to save themselves the time and effort of shopping, food prep, etc. They gain time back with the help of a simple app. Their priority of eating healthy is simplified by a click every morning, and ultimately gives them precious time back to pursue other important items.

CONFIDENCE

We can all create priority lists and creative solutions. Building the confidence to execute them is a little different. This comes with time, trust building, and a bunch of other subjective factors. It’s hard to walk into a new job without relationships and credibility and announce, “My health is really important to me, so I’m going to disappear every day for an hour to go running.”

However, once you’ve built up the confidence that comes with proven work impact and have some relationships in place, it becomes much easier to not have to explain or justify yourself.  

It can be awkward sometimes when I’m the one walking out of the office at 5:30 p.m. and everyone else is going to crank out another hour or so before heading home. I know I arrived hours before them in the morning, and that it’s not the hours that truly matter—it’s the overall impact we make. However, it takes confidence to say to yourself, “I’m executing on my priorities. They may not be anyone else’s, but this is what works for me.”

DETERMINE WHAT’S IMPORTANT TO YOU

Review your list of priorities and determine what’s causing you stress. Perhaps health is on your list, but you haven’t made any time to exercise. Or perhaps you want to sit down with your friends or family at least three times a week to share a meal. Figure out where you are falling short on these priorities, and then edit your behavior to make them happen.

This often comes with a bit of confidence building. If people have certain expectations of you (typical hours worked, always bringing homemade muffins to a team meeting, etc.), you’re going to have to reset those expectations. Do it with confidence and move on. If you’re feeling good about your choices, don’t sweat their expectations. Trust me, you’re thinking about it way more than they are.

Whether you are a parent, recent college grad, or anyone in between, we all have jam-packed lives. However, when we can prioritize and determine what’s truly important to us—and then create ways to take some pressure off those efforts—we make our lives significantly more manageable.

If that’s truly what we call being a “bad mom", then I’m perfecting being the worst.  

Christina Luconi is Chief People Officer for Rapid7. Follow her on Twitter: @peopleinnovator.

Image via Unsplash

At some point, almost everyone wants to start a business (99 percent of San Franciscans do). But remember, as the late, great film star Rex Harrison once said, "Exhilaration is that feeling you get just after a great idea hits you, and just before you realize what's wrong with it.”  

When it comes to startups, realizing what’s wrong means figuring out how the hell you’re going to make your big idea happen.

If you’ve decided to venture into VC funding as part of that process, here are the big do’s and don’ts to make sure you get what you came for.

DO: VET YOUR IDEA FOR FUNDABILITY

A solid $20M per year business with 20 percent margins is great for an entrepreneur, but terrible for a VC.

VC funds are not built for this type of return. They would rather push the business toward (or even off) the metaphorical cliff in hopes of reaching $200M in revenue over seeing you survive safely as “the living dead.”

This isn’t because they are mean. It’s just the nature of venture investing and the way these funds are designed. They have a job to do, and earning competitive returns requires them to consistently hit home runs.

You need an idea that has the potential to be a billion dollar business. And unfortunately, not every idea has that potential.

DO: ENSURE YOU’RE READY FOR VENTURE FUNDING

Venture capital today should really remove the word “venture”.  

Most venture capitalists want to invest in businesses that are already up and running with some sort of traction (be it users, revenue, profits, or all three), with much of the risk from the old Apple and Intel days removed.   

You’ll need to have gotten somewhere on your own first and have something to show for your big idea. Not to mention, raising funds takes time.

DO: BUILD ONGOING RELATIONSHIPS

Others might caution against it, but I believe that there’s nothing wrong with starting to build relationships as early as possible.

It can be smart to go in early — knowing you’re early — just to meet with potential investors to tell them what you plan to do. The key is that you come back nine months later and prove that you did it before asking for money.

Investing, much like life, is very relationship-driven. If you don’t have relationships with VCs in place, you need to build them — and that won't occur overnight.

DON’T: ASK FOR AN NDA

Whether you’ve heard this a thousand times before or not, never ask an angel or VC to sign an NDA just to hear your idea. No VC will do it, and all it does is make you look green and inexperienced.

In reality, your idea is not special. Get over it. Ideas are a dime a dozen. The value lies in actually having the skill and hustle to make your idea happen.

Whenever a new entrepreneur asks me about NDAs, I always tell them to take their business plan, make copies, and go around and drop it in every coffee shop they see. They could even stand and give presentations on the street corner and it wouldn’t matter.

You, and only you, are the one who has decided to devote your entire life to this idea in the hopes that it will work.

DON’T: THINK THAT ANY INVESTOR IS A GOOD INVESTOR

Just getting an investment does not make you successful, prove you’re smart, or mean you’ve earned a place in the club.

Let’s face it, most venture investors have likely been providing worse returns than the market for decades. There are usually only a handful of great ones who can really make a difference in your business from start to finish.

Make sure to do your homework, talk to past investments, current portfolio companies, and perform your due diligence. Which isn’t to say you don’t take the investment in the end. But at least you’ll go in with a clear view of who you’re getting in bed with.

DON’T: PAY ANYONE TO RAISE MONEY FOR YOU

It’s never a good idea to pay someone to raise money for you — or even close the deal.

Good investors won’t want to see their money going toward someone brought in just to work a deal. In fact, almost every single investor document I’ve signed has a “no success/finder’s fee” clause in it.

Spending money on something like this will do nothing to move your business forward, and a startup that’s raising funds likely needs every single penny it can keep.

There you have it: the six best do’s and don’ts of VC funding for your big idea. Put these into practice if you’re headed toward the funding stage and be sure to let me know how it goes!

Carlos Cashman is CEO/Managing Partner of OrionCKB. Follow OrionCKB on Twitter: @OrionCKB. 

Back in 2008, it was uncommon to find a venture firm that focused on early-stage investing. It was even more uncommon for a venture firm to have a college student as its founder. But this is exactly what Krishna Gupta, Romulus Capital's Founder and Managing Partner accomplished.  

Today, we take for granted things like Rough Draft Ventures and the Dorm Room Fund, which are student led but with funds that are ultimately supported by larger VC firms. Few students have actually gone on to raise their own fund.

Timing was also interesting for Gupta to start this new fund, since the economic conditions were not ideal in 2008. However, in down times there are opportunities, and it ended up being perfect timing for Gupta, as he was able to fund several great companies. Read more in the interview below.

Keith Cline: Tell me about your background.

Krishna Gupta: I was born and raised in the suburbs of Chicago. My parents came to the U.S. from India in the early 1980s. My mom studied computer science and worked in the telecom industry for Bell Labs, Lucent, and now Nokia.

My dad was an electrical engineer, who was part of the first group to implement six sigma at Motorola. He then started his own consulting firm on helping other companies implement six sigma and later was part of a startup during the internet boom of the ‘90s.

The internet bubble burst in 2000/2001 and I saw firsthand the downside of entrepreneurship and what it does to a family.

However, entrepreneurship was in my blood, through my immediate family and my mother’s family. I remember starting businesses when I was a kid, such as a neighborhood store making crafts. It was gratifying to create something and save profits to share among my “employees”. I remember the first profits we collected, we used to buy a pack of peanut M&Ms from a neighborhood vendor.

I came to the northeast to attend boarding school at Phillips Andover. I chose the school because it was one of the top schools in the country and they had an open ecosystem for learning. It was a place where I could explore my academic interests and passions.

I've always had a love for math and competed in math competitions through middle and high school. I was selected as a finalist for the U.S. math olympiads multiple times and was in the top 50 across the country for my year. It was a lot of fun, but you ultimately have to be in the top six to be selected for the U.S. team that goes to the International Math Olympiads. Since it was essentially impossible that I was going to reach that goal, I started to branch out and explore other interests.

I started honing my writing skills and made a film in England. The filmmaking experience also gave me another crack at entrepreneurship - I had to raise capital from professors on campus - so I could go abroad to make the film.

After Phillips Andover, I attended MIT to return to my science roots and be at a place that was world-class in both engineering and business. I knew I wanted to start a company, and that’s a key reason I chose MIT. I was allowed to take classes with the MBA students along with my engineering classes, which was very rare. I graduated with two degrees: Management Science and Materials Science and Engineering.

KC: What did you do for work as an intern at JPMorgan?

KG: For two summers, I was very fortunate to be the lead analyst on two billion-dollar transactions. During the first summer, after my sophomore year, I worked on Verizon Wireless’ acquisition of Rural Cellular Corporation. The lead analyst on the deal left the firm and they gave the work to me.

When I returned the following summer, they already knew I was capable of handling the work and they assigned me to be a lead analyst for the sale of The Weather Channel to Bain Capital, Blackstone Group, and NBCU.

KC: How did you get into venture capital?

KG: At MIT, I wanted to start a company, and I met a lot of like-minded people with similar ambitions. As I started looking into the ideation/company-building process, I realized there was no one to help build foundations of companies. I noticed that a lot of VC firms were just lottery machines and were good at pattern recognition. They would provide the capital, but they weren’t always involved in the foundation of actually building the business. I found myself working with different student entrepreneurs and thought I could add value to multiple companies as a seed investor.

At that point in time, seed investors were pretty uncommon. There was First Round Capital, Founder Collective, and maybe one or two others. It was especially unusual for someone of my age to start a venture fund back then, too. It took me a year and a half to raise our first fund of $850K. Our initial focus was on companies out of MIT and Harvard.

In parallel, I graduated from MIT a semester early in 2008. I was recruited to work at McKinsey as a strategy consultant. After I signed the offer letter, the financial crisis hit and the world was in a tough place. The firm ended up deferring a bunch of the new hires by six months. Thus, I had 12 months before I was scheduled to start working at McKinsey.

The first six months were spent traveling across the world and raising capital to close out our first fund. The second six months were spent building the foundation for Romulus Capital.

I thought I could balance both jobs in terms of Romulus and McKinsey. I was wrong and had to make a decision. I chose Romulus.

It ended up being great timing. In Boston, it was difficult to find seed investors who could write smaller $40K checks and I was helping to fill a void in the market. Plus, in my opinion, the bottom of the market is the best time for any entrepreneur to start a company. You have to develop a leaner and hungrier mindset, which matches up with our investment philosophy to be conviction driven and not market driven.

KC: What companies are currently in your portfolio?

KG: ClassPass, Cogito, Disruptor Beam, Ginger.io, Placester, Smart Lunches, The Tap Lab, Humanyze, E la Carte, and others.

KC: What stage of investments do you primarily target?

KG: We like to be the first money in for a company, in terms of their seed or Series A round of funding. Our first fund had a mix of B2C and B2B companies.

Our second and now third funds tend to be more B2B focused, with technology companies across a variety of industries such as real estate, healthcare, retail, construction, etc.

KC: What are the top traits you look for in terms of investing into a company or founder?

KG:    

• Large market
• Hunger and resilience - I have a hard time working with people who don’t have the same killer instinct
• Engineering backgrounds bias - I tend to like people who are technical
• Team fit between technology and the market
• Sustainable advantage - There is no such thing as first mover advantage anymore. Others will raise money and compete against you, so what will make this company survive over others? Some will succeed based on relationships, others will succeed based on their technology. Take machine learning. It is not a revolutionary concept, but the team that has the deepest experience dealing with a problem will likely win. For example, ginger.io was working on solving a problem for five years before they raised capital from us. They are now 12 years in and no one has the same level of depth and accuracy dealing with data sets for mental health as this team has.​

​KC: What is the current fund that you are investing from?

KG: We just closed our third fund, which is our largest at $75M.

KC: What excites you about the current market in Boston?

KG: From a talent perspective, it is hard to beat Boston. The talent pool is highly intellectual and there’s an extremely dense amount of world class human capital here working to solve complex problems. The ideas here are adding real value to the world, versus another consumer photo sharing app.

The [Silicon] Valley has a larger amount of talent, but it all feels very commercial. It’s all about deal making and “who is in your round.” Still, there’s a lot Boston can learn from the Valley.

KC: What companies in Boston, outside of your portfolio, do you find interesting?

KG: I’m a fan of Wayfair and several of the cybersecurity companies located here.

KC: Greatest misses. Are there any companies you passed on that you wish you hadn’t?

KG: I don’t think we’ve missed out on anything major yet. The larger companies in the Boston tech scene, like DraftKings, didn’t match up with our investment strategy.

KC:  Who do you admire or who has been the greatest mentor for you?

KG: I don’t really have a mentor, although I do admire a lot of people in my industry like John Doerr (Kleiner Perkins Caufield Byers), Michael Moritz (Sequoia Capital), Josh Kopelman (First Round), and Hemant Taneja (General Catalyst).

KC: Outside of being a VC, what are you personal interests or activities?

KG: I am a big sports fan (football, basketball, tennis, and cricket). I have been spoiled, as I watched the Chicago Bulls as a child during the Michael Jordan era, and the Patriots won their first Super Bowl when I moved to Boston and have obviously been on a run since.  

I’m also a student of political and military history. I also find the arts a great way to relax and discover.

KC:  What was the last book that you read?

KG:  The Everything Store: Jeff Bezos and the Age of Amazon

KC:  Are you involved in any charitable organizations?

KG:  Not yet, however I do think there will be a time when I start my own charity. Perhaps something that would help orphanages. If you think about it, orphans are missing their parents, which is the biggest missing support foundation anyone could have. When you are deprived of something of that magnitude, it drives a hunger that is often times correlated with what makes entrepreneurs successful.

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

In my last post, I discussed how to stand out with a content marketing strategy. Now we’ll talk about what happens at scale. Because once your strategy hits and you've created a stand-out in the industry, the opportunities to increase exposure will rise. People and press will want to know your organization’s takes on other hot topics and on other ways your organization can solve industry problems.

But researching, writing, refining, and getting these pieces to market can take a lot of time and money. So while being the go-to industry resource is absolutely the position to be in, you also need to consider scaling your content.

DRIVING YOUR CONTENT'S VALUE

Scaling content means getting more value out of the initial investment, like taking a keystone piece and repurposing it into other forms, thus getting more benefit for incremental investment. Why do this? Not only to gain additional returns on your initial costs, but also to cater to different learning styles and different points of the funnel.

Virgin Pulse, for example, released a State of the Well-Being Industry survey report in 2015. The report presented influential data about where the industry was heading in a detailed and informative way. But not everyone would take the time to read the report in its entirety, so a press release summarized key findings, a slideshare was created, blogs were written about it, press picked it up (some featured the infographic created from the findings), and the content was synthesized into webinars, ebooks, tip sheets, portions of sales presentations, and more.

For Virgin Pulse, this meant getting a lot of traction and extra value from investment in one piece. It also meant hitting prospects at different points in a buyer's journey. Personally, I've seen abbreviated pieces like ebooks, tip sheets, and webinars work well at the top of the funnel. They hit prospects with information in the way they want to consume it, and in the time they have (i.e. not much, if they don’t know much about you or the problem you’re helping solve).

(DON'T) ABIDE BY THE RULES

But once buyers start researching and consuming content, really thoughtful pieces like white papers, survey reports, in-depth blog posts, and similar pieces work well in the middle of the funnel. When a prospect is in the middle of the funnel, they want to learn more in-depth information, and they’ll start to want to know specifically how your organization will solve their problem.

This said, there are no hard and fast rules here. At one of my previous companies, a thoroughly researched and well-written report was the all-time top of funnel lead generator. So see what works for you and your organization, but always think about how you can get more value out of your content investments by scaling them. Doing so is simply a smart use of time, money, and resources.

Modern, high-functioning marketing teams are nothing if not publishing shops, but startups need to be smart about bandwidth. Scaling content means using resources and optimally spending to get a greater return, while also helping increasing the assistance given to prospects with different learning style and time constraints.  

Shawn LaVana is passionate about helping marketers market better. He leads the marketing team at TempAlert, having previously scaled high-growth startups including Virgin Pulse and ShapeUp. Follow him on Twitter: @shawnlavana

Multiple times a week, I connect with a variety of people in my company who are looking for career coaching or advice. Often, these are conversations with very talented, high-performing people. However, I’m often surprised by the lack of self-awareness or confusion about where they stand within the organization.  

IT’S LIKE DATING

When people don’t know where they stand, they get uncomfortable.

It’s not unlike dating. You are in a relationship with someone you really like, and you’ve decided to commit. And yet, they haven’t been forthcoming about their feelings. When this happens, sometime we (or at least most of us, from what I can tell) become insecure, and begin to make decisions we wouldn’t necessarily make.

We might ask our friends what our partner is thinking. We might start exploring other options. Bottom line: we might just sabotage the whole relationship, just because we didn’t have the courage or self-awareness to ask, “Where do we stand?”

I’d suggest the same behaviors apply within the business environment. You’ve made a good impression and you got hired. You believe you are off to a great start—you’ve bonded well with your team, you add value in meetings, and you are executing on your deliverables.

But does your manager feel the same way? If you don’t actually touch base with your manager and confirm that your own assessment of your work is on track with hers, you’ll be in a continuous state of wondering. Maybe they’re expecting you to execute on a different set of deliverables. Or maybe they aren’t even completely aware of what your results look like. Of course, a strong leader won’t leave you guessing. She or he will provide a steady stream of real-time feedback.

Just for the purposes of this discussion, though, let’s focus on these managers who don’t.  

HOW TO ASSESS WHERE YOU STAND

Take a deep breath, gather all your confidence, and prepare for a direct conversation. Put some time into preparation—outline both your successes and areas for improvement—around the following areas to set yourself up for a healthy dialogue.

One additional helpful hint: listen with an open mind. Ask questions for clarification, and don’t argue. You are seeking to learn, not debate.

Skills: Do you bring a solid set of skills to the table? Having a strong grasp on the fundamentals of the job is typically the major component that scored you the role in the first place.

Just make sure your interpretation of how your new company wants you to execute in your role lines up with their expectations. Set clear goals together, and communicate often and openly on progress.

Attitude: Do you grab a shovel and dig in? Do you focus on your team’s success in addition to your own? Is your Emotional IQ just as strong as your skill set? Do you focus on bringing solutions to the table, not problems?  

If you're nodding yes, you’re probably scoring pretty high attitude points.

Aptitude: It’s one thing to come to work with a good attitude and crank through your list. It’s another to show the capacity to learn and grow. It’s hard for managers to be inspired to give you more if you aren’t comfortable pushing yourself to develop and grow.

Culture Fit: What does your company truly value and believe in? You can be the greatest worker on the planet, but if you don’t subscribe to your company mission and belief system, it’s hard to be fully invested.

Impact: What impact are you truly adding to the business? Can you draw the line between what you are contributing and how it’s affecting the business? Growing profit and the bottom line are the only reasons a business thrives. Know your place in that element.

We all show up to work believing we are bringing our best. However, if you don’t know where stand, it’s easy to feel confused, uninspired, and perhaps even a little insecure.

The good news? You are likely in a way better relationship with your company than you realize. Sometimes, you just need to push the conversation and ask.  

Christina Luconi is Chief People Officer for Rapid7. Follow her on Twitter: @peopleinnovator.

I launched VentureFizz in July of 2009 and about two months later, I started sending out our weekly email. Over time the email has evolved quite a bit, but the mission remains the same: It's your once a week go-to for staying connected to the Boston tech scene.

When I go to an event and introduce myself, I am still always amazed at how many people say, “Your name appears in my inbox every Monday!” It has been really fun to watch the distribution list grow from what started out as a grassroots effort.

I am proud of the feedback and how people find the content every week incredibly useful. But our design has been outdated. In fact, when we conducted a reader survey a few months back and we had over 600 people share feedback, about one-third of it was related to the weekly email newsletter. It was too long, hard to read on mobile, and unorganized. It was clear that redesigning our weekly email was long overdue, and it immediately became a top priority.

It was good timing, since we had tackled some other important projects. For example, at the end of last year, we launched the new design of our website. Then, we released two new daily emails, Daily Job Alerts and VentureFizz Daily, giving our audience different options to consume our content. (If you don't already subscribe to our weekly or daily emails, subscribe now!)

Having the new emails gave us the flexibility to change the format of our weekly email. After taking a deep dive into the analytics, it was obvious that people were consuming the commentary I write every week at the top. But after that, the CTR dropped significantly.

The new design offers a more visual way of consuming my opening commentary. It still includes other aspects of the email that people find useful, like the Deals section. We've removed the Jobs and Stories sections, since they're a duplication of our new daily emails (Daily Job Alerts and Today’s Top Stories).

We hope you like the new design! If you want to share your feedback, please send me an email or click here to send a message through our site. We’d love to hear from you!

I thought it would be fun to review the evolution of our weekly email and get a little nostalgic. Below are four images of our weekly email through the years. Enjoy!

HELP US SPREAD THE WORD ABOUT THE WEEKLY EMAIL'S NEW FORMAT. CLICK HERE TO SHARE IT ON TWITTER. 

Our very first weekly email on September 2, 2009

Our redesign on September 3, 2013

Last week's email on July 5, 2016

And now... today's email featuring our new design!

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

John Pearce is Co-Founder and Operating Partner at _Underscore.VC, one of Boston's newest venture capital firms.

Pearce is humble - the type of individual who doesn't look for recognition and instead lets his success speak for itself. He has an amazing track record of success in leadership roles for many of Boston's most successful companies. He was CEO at Demandware and CFO at companies like Actifio, AppIQ, SilverStream, and Watermark. (Actifio is one of Boston's unicorn companies and all the others have successful exited). 

The good news for Boston enterpreneurs is that Pearce is now applying his 25 years of experience to help build more anchor companies locally, along with his co-founders Michael Skok, C.A. Webb, and the rest of the _Underscore.VC team. Read more in the interview below. 

Keith Cline: Tell me about your background as a child and where did you grow up?

John Pearce: I grew up in Australia. My father was a businessman. His first business failed and the biggest lesson he learned from that was not to have a weak partner. He sold his second business when he retired at 72.

As I was growing up, I was exposed to meaningful conversations around the kitchen table about building the business, like how to survive the next month and pay the bills. The notion of building and running a business became central to my interests.

KC: What brought you to the U.S.?

JP: I came to the United States nearly 30 years ago to launch a business in California for an Australian investor.

My introduction to disruptive business models, which I did not realize at the time, was building a book distribution business based on a series of health and diet books. We sold direct to drug store chains like Walgreens and others, versus selling through traditional publishers as the middle-man.

I was later introduced to David Skok, now a General Partner at Matrix Partners. But back then, he was the CEO at Xionics in the UK, and Michael Skok was on the board. I moved to London and we worked together to turn the company around. Hambro International Venture Partners was an investor in the company and that is how I met Rich D’Amore, who ended up being one of the founders of North Bridge.

I came back to the U.S. and continued working with David on the two companies he founded: Watermark Software (the spin out of Xionics, later acquired by Filenet/IBM), and SilverStream Software (which went public in 1999). Rich and North Bridge were involved in both companies and subsequently at AppIQ and Demandware, where Michael invited me to jump in. Actifio was the next connection.

Over my 25 year career, I’ve had the opportunity to work with so many great people and entrepreneurs. I was also fortunate to work in a variety of roles such as CFO, VP of International Business and CEO. I was able to build upon each experience along the way.

Pearce hanging out at the Saturday Farmers Market on Martha's Vineyard

KC:  What convinced you to become CEO of Demandware in 2006?

JP: Michael Skok called me about the opportunity as I was walking on a beach in Florida. You could say the rest is history. But to rewind, at that point in time, the industry was mainly on-premise software from companies like IBM and ATG for the eCommerce sector.

I was impressed with the vision of the company’s founder, Stephan Schambach, and his experience building companies. It was the very early days of SaaS and there was a public SaaS company, Taleo, that I did some research on. I did some back of the napkin math on the opportunity and the data supported my decision and gave me the final conviction to join.

Of course, I did not know what I did not know.

KC: Can you share some of the details that contributed to Demandware’s success?

JP: When I joined in 2006, the company had six beta customers and was in the early stages of trying to figure out its business model. It was the early days of SaaS and the existence of mission critical enterprise SaaS applications.

At Demandware, we were powering a retailer or a brand’s eCommerce site. If their site went down, their revenue went along with it. Thus, they needed 100 percent uptime and - thanks to great people like Wayne Whitcomb and Ulrike Mueller - Demandware’s co-founders and their teams delivered over and over again.

I was lucky to have a fabulous team to support us. Our founder, Schambach, had a tremendous vision. Jeff Barnett, Demandware’s COO, was in the trenches helping figure out the revenue model, and we didn’t have an obvious answer. And as I mentioned, Whitcomb’s team built the backbone to support our customer’s uptime expectations.

Along the way we brought in people like Virginia Alinsug to lead services and Troy Brown, who had the retail and eCommerce DNA to help take our business to the next level. We’re privileged to now have all these people in our Commerce Community and _Cores, helping with some of our first investments like Mautic and Zaius.

Ultimately, at Demandware we figured out that our business model needed to be aligned with the best interests of our customers. We positioned ourselves as a partner with our customer and we would charge a percentage of revenue that went through our platform - we called the model “gross merchandise value” or GMV as it’s become known in the industry. This new idea was a tough sell at first, but over time it caught on.

Since our revenue was based on our customers’ success, it really affected us as a company. We had an amazing team at Demandware and in those day’s we had an internal theme of “no customer left behind.” It became core to the company, its culture and success.

KC: Why did you end up joining Actifio?

JP: I met and worked with Ash Ashutosh (Actifio’s CEO and Founder) at AppIQ, which was acquired by HP. Ash is a great entrepreneur with incredible vision, who is very customer and market centric. He had identified a problem that I could relate to. It was the complex problem of managing storage and he was solving it with great technology. But we knew it wasn’t going to be easy competing against companies like EMC.

I joined as the company’s CFO in 2011. I was excited to be part of the team and it was a great opportunity to disrupt the incumbent solutions out there. I’m proud of what we were able to accomplish, as Actifio is now one of Boston’s anchor tech companies with people like David Chang, Mike Troiano, and Jim Sullivan at the helm. It will undoubtedly continue to thrive.

KC: Why did you decide to get into venture capital as an investor?

JP: I never thought I would get into venture! But that is part of life, finding new experiences that you want to explore. Last year, I got another call from Michael Skok as I was walking on the beach looking to catch up. (I guess I should avoid his calls when I’m on the beach.)

Michael was on his listening tour and looking for some honest feedback on the venture industry and my experience dealing with investors. Since I had been involved in raising money several times from many of the best firms such as Matrix and Andreesen, he wanted my opinions on what worked well and what didn’t work out so well.

A one hour coffee meeting in Boston turned into a three and a half hour discussion with lots of drawings on napkins. I then started looking at some of the disruptive new investment vehicles like AngelList, and changing forms of funding coming from crowdfunding platforms, and incubators, and accelerators. It’s an interesting time in the venture industry and certainly a time for innovation.

Michael and I decided to become partners and met with many other entrepreneurs, which ultimately led to the thesis for _Underscore.VC. We started by working on some joint investments that we later rolled into our initial $75M seed-to-A venture fund. We were very pleased with the reception and have been backed by an outstanding group of Limited Partners, including some of the best children’s hospitals, leading academic institutions, and global foundations.

KC: What are you targeting in terms of terms of investments at _Underscore.VC?

JP: People are the cornerstone to our decisions. How do they think? Can they keep up with and lead the pace of innovation and build a sustainable company? We are focused on being the first institutional capital in, and I’m really excited about the value we can bring with our Community and _Cores who are aligned as partners with us to help at each stage of building great companies.

Beyond people and stage, our core focus is Cloud Intelligence. Back in 2003, Michael developed an investment thesis entitled, “Everything as a Service,” which has proven to be farsighted with decades of investment opportunities ahead.

KC: How is _Underscore.VC differentiating itself from other VC firms?

JP: First off, we bring a community of entrepreneurs and investors aligned to help the founders we invest in. In doing this we’ve created a fund that has aligned itself fully with the interests of the founders.

Within our community, we have built out something which we call _Cores. They are curated groups of peers organized by domain, stage, and skill/function. They have a proven track record at building companies and can give back by advising our entrepreneurs.

Our _Core members can earn shares in our investments for the time they are spending as an advisor, becoming partners with us. They also have the opportunity to invest in our companies with us, again as true partners in the fund, on the same terms and conditions on a deal by deal basis.

Although money is needed to scale a company, it is really the advice and the introductions that our _Core members can provide to our entrepreneurs which makes our model an incredible value add.  

In that vein, we’re committed to syndicating with other firms for the good of the Venture Community and of course we’re very committed to Boston. Our goal is to not only build iconic companies that have long term lasting value to the region, but also to bring up the next generation of venture investors from within our firm and from our _Cores.

The _Underscore.VC team

KC: You have announced a couple of recent investments: Mautic and Zaius. Can you share a brief summary on why you invested in each company?

JP: We’re really excited to see our portfolio start to grow and the entrepreneurs behind Mautic and Zaius are outstanding individuals that we are proud to back as they build enduring companies. As we invest, we will continue to post blogs on our website that tell the story of how we got the opportunity to invest in each of our portfolio companies. Those are already online about Mautic and Zaius.

What’s interesting about both of these is that they are in the marketing technology space, an investment area that we see huge opportunity in. As marketing continues to evolve from 1.0 to 2.0, there will be a few great companies building great products to help marketers succeed and allow their customers to increase revenue. We believe that Mautic and Zaius have that opportunity.

Mautic has an an amazing vision, led by founder David Hurley, and its open source approach to marketing automation has already enabled them to experience significant traction with over 50K organizations on the platform, 35-plus integrations, and translations of the platform in 49 languages.

Zaius is looking to solve the difficult single-source of truth problem for business-to-consumer retailers by providing a CRM for them to use that is uniquely built for the scale and velocity of B2C marketers. They already have outstanding customers like Nine West and Moda Operandi and are have a great team based in Boston and Virginia.

KC: What is the meaning behind the name _Underscore.VC?

JP: When we were developing our final name, we thought about how our main job as an investor is to emphasize and highlight the entrepreneurs we work with. We thought that underscore spoke to the fact that our role is to supporting our entrepreneurs and highlighting their strengths.

As we tested the name with our community, we got great feedback for a lot of reasons. My favorite has been around a more subtle part of the name: its relevance to the technology community.

As a Cloud Intelligence-focused firm, the underscore in the name refers to a previously common coding practice. Variables in programming used to use underscores to declare the variable. As a firm, we hope to be the variable that underscores great entrepreneurs. We're making a nod to those who came before us and those to come - connecting them.

KC: What excites you about the current market in Boston?

JP: The Boston tech market is a great place to be. The people are level headed and there are so many great academic institutions with people who are building wonderful things for the future. Our goal is to identify the best opportunities and provide them with the right knowledge and resources to scale and grow.

KC: Are there any companies in Boston outside of your portfolio that you find interesting?

JP: Yes, we have a lot to be proud of in the Boston tech scene. I mentioned Actifio earlier and we have a great list of companies being built. Some that I identify with are Onshape, being led by Jon Hirschtick and John McEleney. Veracode is being led to the next level by Bob Brennan. I am interested to see how Andy Ory’s new 128 Technologies evolves and Simplivity, led by Doron Kempel. And there are many more.

KC: Outside of being a VC, what are you personal interests or activities?

JP: Although my dermatologist does not like it, I like to spend my free time with my wife of 28 years and children golfing, boating, and - you guessed it - being on a beach.

Pearce with his wife, Kathryn, during a function at Ocean Reef in Key Largo, Florida

KC: What TV shows do you watch and what type of music do you like?

JP: I don’t typically watch anything that is not DVR’d anymore. I am a big Blacklist fan.

You might be surprised that I love country music and that I find one of the more interesting bands of recent time is Alabama Shakes.

KC: Are you involved in any charitable organizations?

JP: I’ve lived in Andover for 20 years, and we have had the benefits of that community. I would give a shout out to the great work done by the Boys & Girls Club of Lawrence and the Bellesini Academy in Lawrence.

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.