Insights: Greg Raiz Insights

Greg RaizThis week’s insights are brought to you by Greg Raiz, CEO of Raizlabs, an app company that’s been leading leading in mobile software development since before the launch of the iTunes App Store in 2008.

You may not have met Greg, but we bet you’ve met some of the essential apps he and his team have created, apps like HubSpot, Bloomingdale’s, Rue La La, and RunKeeper, to name a few. Greg approaches app development like he does his team: methodically. Raizlabs is known for their exceptional product management, creative design services, and impeccable execution. But that’s not the only thing that’s driving Raizlabs’ unprecedented growth—it’s their commitment to their people. Building the right team, capitalizing on each person’s skills, and promoting innovation from within…it’s all about the people.

As your team grows, how do you ensure that you all remain aligned around a central vision?

We’ve spent a fair bit of time this year thinking about the culture of the company and how we can align the entire company around a vision and mission. Everyone wants to make a difference and feel that their work is important. We started by creating a high-level vision that we could rally around. It was important that the vision would stand the test of time and allow the organization some flexibility. Our vision statement of “shaping the world through great software” has led us to explore the values that our company felt were necessary for us to execute that vision. These values now guide most of the decisions we make from hiring, to the projects that we take, to the regular feedback we give to one another. Keeping the vision and values central to our process serves as a natural reminder for us. 

What’s one strategy or tactic that you consistently use to support the growth of your team.

Trust, but verify. I think it’s great to give your team a lot of trust and autonomy to grow, experiment and occasionally fail. The key is putting in your own checks to make sure they aren’t failing too much. Keeping track and closing the loop gives you the opportunity to give the person a pat on the back if they did a good job or a nudge in the right direction without micro-managing.

In your opinion, what is the primary role of a manager?

My primary role as a manager is setting up situations where people can be successful. This cuts across a number of things including hiring, company culture, tools and procedures. If I’m doing my job then the team can execute and do great work and it feels effortless. A mentor of mine explained it best; your team is a train, they are rolling along. It’s your job to make sure they have plenty of track and no hazards in the way.

How do you ensure that you stay in lock step communication with your team?

This has been an increasing challenge as the team has grown. It’s easy to stay in lock step with five people but hard to stay in lock step with 50. We have a company Town Hall meeting each week so everyone can get up to speed on the entire business with minimal overhead. Beyond this, I try to have regular conversations with both leads and individual contributors. This helps keep me stay grounded with what’s really going on at the company.

How do you continue to evolve as a leader?

As a leader, your job is constantly changing. One day you’re thinking about hiring, the next you’re dealing with technology questions. The key for me to evolve as a leader is to constantly question if the things I’ve done before continue to make sense as the company grows and changes. The way our company did projects stopped making sense at a certain size and scale. We had to unlearn certain habits and learn new ones. Growth as a leader is being open to change and adapting how I do things as the organization grows.

Greg Raiz founded Raizlabs in 2001, after getting his start at Microsoft. Since then, he’s been working toward his vision of building incredible software, and has helped over 100 companies improve the way they connect with their markets. Raizlabs was named one of Inc.’s 5000 Fastest Growing Companies in 2014.

Want to learn leadership skills from more startup vets? Enroll in Exchange!



Why You Need a Personal
Board of Directors

Sydney Atkins MasonWhy we all need a Personal Board of Directors and how to develop one.

Strong leaders know better than anyone that no one achieves anything alone. A support system is instrumental to achieving team goals, propelling individual career growth, and perhaps most importantly, maintaining sanity.

At a recent Exchange fireside chat, Sydney Atkins Mason, Investment Advisor at Goldman Sachs, shared why her “Personal Board of Directors” has been the most priceless weapon in her professional arsenal. It can be tricky to assemble the right network when you’re not sure what to look for, but Sydney credits her wealth of success to her relationships with three major people – her mentor, sponsor, and coach:

Mentor: Your mentor is the John Keating to your Dead Poets Society, the Socrates to your Plato, the Hagrid to your Harry. A mentor will never dole out the same piece of advice to two different people because to your mentor, you are a beautiful and unique snowflake, with triumphs and challenges that distinguish you from other snowflakes. A mentor helps you to evolve over time. This relationship is frequently a two-way street; the mentor is a catalyst for mentee growth, and mentors get the “warm fuzzies” from helping someone out.

Sponsor: Unlike a mentor relationship, a sponsor relationship is linear; your sponsor will catapult your success–if you play your cards right. Your sponsor can help you move forward in your career by publicly vouching for you, endorsing your skills and strengths, or even open doors you didn’t know existed. This person does this purely because they believe in you and, often, there is no way to repay them. This should be someone you deeply respect and admire, who can become your ally as you evolve in your career. Your success is your sponsor’s success, but be sure you pay it forward and become a sponsor to someone else. Don’t get greedy. You don’t want to be that guy.

Coach: A coach is your sounding board for any seemingly “stupid (functional) question” you have. Need help using the company database? Ask your coach. Having trouble understanding some jargon? Ask your coach. With your coach, all your questions are valid concerns. Your coach is who you rely on for your most immediate and basic job-related concerns.

Look around at who you know today and whether there are people in your midst who might naturally fill these roles for you. Have an open conversation, letting them know why you appreciate their advice and what your ask is, but most importantly, invest the time in developing those relationships. Now go! Insights: Ben Carcio Insights

Ben Carcio

This week’s insights are brought to you by Ben Carcio, CEO of Promoboxx, a company that connects brand manufacturers with independent retailers to help retailers become better marketers. Since 2010, Ben and his team have expanded Promoboxx’s capabilities to help industry-leading Fortune 500 companies like, Chevrolet, Pepsi, and Timberland.  Ben lead by example to create alignment among his team, sharing his own experiences to support the continued development of each individual in the company.

What’s one piece of advice you wish someone had given you as a new manager?

Never mess with someone’s paycheck. Its sounds silly, but as leaders we sometimes forget that we’re providing our employees with a livelihood. When things are stable nobody thinks about it, but when there’s any hint of instability all other leadership tactics fly right out the window. For example, when I was running a 25 person painting company in college, I was a day late on making payroll and 6 of my best guys quit to join another “more stable” company. This lesson sticks with me every day.

As your team grows, how do you ensure that you remain aligned around a central vision?

Communicate the vision. Communicate the vision again. Then communicate the vision some more.

In your opinion, what’s a manager’s primary role?Promoboxx Team

Below average managers assign subtasks and authorize vacation time.  Amazing managers are leaders, and leaders empower their employees to do more by setting a clear vision, providing the right resources, and building a great support team around them.

What’s the biggest leadership challenge you’ve had to overcome? How did you do it?

Lack of experience. One of the best ways to lead is through the sharing of personal experience with employees. But with Promoboxx I’m hitting some new challenges that I’ve never experienced before. So, I’ve found the best way to overcome this is to borrow from the experience of others. You can do this by reading the hundreds of amazing leadership blogs out there, or even better, by reaching out to real live mentors for some 1:1 help over a coffee or beer.

Ben Carcio is a startup veteran with over 12 years of online brand marketing experience. He founded Promoboxx in 2010 and has been working hard ever since to provide retailers, like GE, Chevrolet, Pepsi, and Nestle, with the digital marketing tools they need to transform their brand. Ben has been known to share his insights with the startup community at the annual Boston Tech Co-Party, on the Promoboxx Blog, through, and beyond.

Want to learn leadership skills from more startup vets? Enroll in Exchange!

Rachel WaldmannRachel Waldmann
Content & Community Specialist

Top 10 Leadership Posts of 2014

Effective leadership isn’t about who you know, or what your job title is. It’s about inspiring greatness by creating a clear vision and aligning your team to achieve results. Great leaders, by definition, take matters into their own hands to drive their success, and this means actively continuing to invest in self-improvement and personal growth.

We know you’re busy, and don’t have time to scour the Internet for the best leadership articles, so we did it for you. We searched high and low for great leadership reads and carved them down to our top 10, and wrapped them up with a big bow! This compilation of the ultimate leadership articles of 2014 is our gift to Boston’s incredible community of achievers, creators, and builders. Happy New Year, and we’ll see you in 2015!

1. The 100 Most Creative People in Business 2014: Fast Company

This one’s thrown into the mix to inspire you. As you wrap up 2014, think about who you want to become as you move on to 2015. This list of creative people in business includes founders, Fortune 500 presidents, Hollywood actresses, and everyone in between with motivating stories of success to learn from.

2. How Great Leaders Inspire Action: TED, Simon Sinek

In this TED Talk, author Simon Sinek communicates his model for inspirational leadership, all stemming from the question, “Why?” He uses real-world examples to help his audience become motivating, action-oriented leaders. At, we believe in the power of giving people a compelling reason to back up their actions,  and Simon generously shares this perspective in his electrifying talk.

3. 7 Things Great Leaders Always Do (But Mere Managers Always Fear): Inc.,    Bill Murphy, Jr.

This article reinforces the fact that managers and great leaders have different skillsets, both of which can be taught. Leaders value honesty and transparency, as well as building relationships with team members, seeing them as people rather than job titles. They understand that team dynamic is just as important as driving results.

4. Leading Your Team into the Unknown: Harvard Business Review, Nathan Furr & Jeffrey H. Dyer

As companies transform in size, location, and scope of services, it’s up to team leaders to provide a sense of stability. As a leader, you are the Indiana Jones of this operation, leading your team into the dark unknown and maintaining focus to come out the other side. Clarify a vision, set challenging yet attainable goals, and take risks.

5. This Unusual Startup Strategy Led to a $200 Million Acquisition by Microsoft in 18 Months: Inc., Larry Kim

MicrosoftIn this Inc. article, Wordstream founder and CTO Larry Kim interviews Acompli’s co-founders about their startup strategy that resulted in a crazy lucrative acquisition in record time. For them, it was as simple as defining the vision and focusing all of their priorities on achieving (and maintaining) that vision.

6. The Boring Trait Google Looks for in its Leaders: iDoneThis, Walter Chen

Nobody does leadership like Google. In recent years, Google has been focusing on developing Project Oxygen, their own analysis of what makes their managers successful. The verdict is in, and according to Google’s findings, predictability is among the traits most heavily associated with fantastic leaders. We never would’ve predicted that!

7. Proven Ways to Earn Your Employees’ Trust: Harvard Business Review, Carolyn O’Hara

When managing individuals, establishing trust should be one of your top priorities. In this Harvard Business Review article, Carolyn O’Hara maps out the do’s and don’ts of building relationships with the team. Spoiler alert: you don’t need to do trust falls in the breakroom to facilitate great working relationships.**

8. I Sold My Google-Backed Startup for $75 Million Yesterday– and I’m Scared to Death: Inc., Dave Balter

IDave Baltern this Inc. article, serial entrepreneur (and founder!) Dave Balter provides a candid look into the challenges that come with a rapidly expanding business and gives advice to leaders managing teams during these tumultuous times. For Dave, it was all about clarifying the vision and then driving it home. We think he’s an all-star genius…but we may be biased!

9. Being a Good Manager: Overcoming 5 Common Myths: Huffington Post,     Sara Hershfeld

According to Certified Behavior Analyst Sara Gershfeld, becoming a great leader is about catching yourself in the act of unproductive behaviors and correcting them. She provides guidance on how to handle leadership challenges in a way that promotes team success with just a few simple behavior modifications.

10. 10 Fastest Growing Companies in Boston: Inc., Anna Hensel

Boston is one of the most talented and rapidly expanding startup communities in the country and we’re honored to be a part of it. Growing by 3,860%? This list of 10 fastest growing companies is equally impressive as it bewildering.

** does not promote, facilitate, or otherwise endorse any office horseplay, including, but not limited to, trust falls.

Exchange Grads: Exchange, On!

Exchange Quote

Completing 55+ hours of management development on top of demanding jobs is no small feat!

On Monday night, we celebrated the fourth graduating class of Exchange – our leadership program – with participants from WordStream, Grasshopper, CitiCenter, Smarterer, Intrepid Pursuits, Raizlabs, HubSpot, and TurningArt.

Exchange Program 4 PhotoThroughout the six full-day Exchange sessions, managers developed key leadership behaviors, learned new management tactics, and created close peer relationships to take their skills to the next level. From digging deep to realize their unique growth opportunities, to supporting each other’s goals along the way, this group truly excelled together.

Putting a fiscal value on organizational health is hard to do, which sadly often leads companies to wait too long to invest in their high-potential new managers. Emerging leaders are invaluable, and more often than not, the skills that make a great leader – assertiveness, ability to motivate, and make decisions – need to be cultivated to truly flourish.

“Exchange is the best thing to happen to me professionally.”

The managers who joined this Exchange class are people who motivate and empower their teams, confidently making decisions and facilitating company growth. Today, we’re confident that these new Exchange grads have become true leaders and we can’t wait to see what they achieve next in their companies.

So, congratulations to Program 4–your dedication to becoming more effective leaders has truly impressed us, and we encourage you to take the tools you’ve learned and continue applying them in your everyday lives. Keep on Exchanging!

Exchange Program 4 Companies