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The Bolster Insider

Advice and insights for hiring and scaling executive talent, curated by the experts at Bolster.
We asked our team of executive recruiters to share the hiring trends they expect to see in 2025.

When to Hire a Chief Customer Officer

A CCO touches nearly every part of the organization, from sales, to product, to marketing. They are a collaborator, a champion for customers, and a strategic thinker that understands consumer trends and demographics.

Revitalize Your Career for the New Year

Whether the new year has you feeling all the anticipation of a fresh start or you’re one of the many individuals impacted by recent layoffs, it’s time to review your career goals.

Procrastinating Executive Development

Enabling executive development can be the key to retaining executives for the long term and helping them to grow with the company, rather than being out-grown by the company.

Recapping Navigating Choppy Waters: A Year in Retrospect

The close of the year is an opportunity to reflect—and report—on progress, learnings, and performance. Are you maximizing the value of your end-of-year reflection?

Bolster’s Year in Review

For Bolster, 2022 was a year of continued progress—supporting a growing number of clients, adding transformational executives to our on-demand marketplace, launching new tools and features, and more.

Bolster Partners with Techstars

Bolster Partners with Techstars to Transform Early-Stage Startups through Unique Access to Experienced Leaders

How To Engage With The CMO

Similar to interactions with all CXOs, you’ll have to capitalize on your moments. Here are our tips on how to gain the most value from your CMO.

Signs Your CMO Isn’t Scaling

Your CMO needs the ability to create space in their day for thinking and analysis, they need to be strategic, and they need to be able to stop doing “one more thing.”

What Does Great Look Like in a CMO?

Great CMOs have some common characteristics and skills. We're sharing some of the qualities a CMO should embody in order to stand out.

Recapping Navigating Choppy Waters: Path to Profitability

Experienced executives shared their stories and offered perspective and advice on leading—and growing—companies during challenging times.

Date Before You Get Engaged: Use Projects as Auditions

Hiring an executive is a major commitment for you and your team—you need to get it right. Short term projects can fill a specific need or determine whether an individual will be a good fit for a longer-term role.

Creating an Executive Job Description

Job descriptions are a key element in ensuring you appeal to the right candidates, so it’s important to write them effectively.

When to Hire a Chief Marketing Officer

Marketing is the key function in building your brand, reaching customers, and increasing engagement. When is it time for a CMO?

Recapping Navigating Choppy Waters: Talent Focus

Experienced talent executives shared their stories and offered perspective and advice on recruiting and retention for today’s leaders.

Bolster Partners with Visible Hands Visionaries Accelerator

Bolster Prime Mentors providing 1:1 coaching through Bolster's partnership with Visible Hands Visionaries Accelerator

Startup Boards: VCs and CEOs Need To Do Their Jobs

A great board is one of a company’s greatest assets. A weak board can kill a company. It’s time to hit the reset button on boards and board meetings.

On Leadership: Execution

Crappy execution is a waste startup leaders cannot afford

Avoid Burnout and Bring Joy to Your Work

Recently, Bolster hosted Charlene Wang of LivingOS.org to share her expertise around avoiding burnout and building a joyful, balanced life.

Best and Worst Practices (Plus FAQs) for Layoffs

Layoffs are bad, but how you handle them makes all the difference. Here are a few best and worst practices for orchestrating layoffs.

Recapping Navigating Choppy Waters: The CEO Perspective

Experienced CEOs shared their stories and offered perspective for today’s leaders.

Don’t Ask Your Board for a Strategy

You want your board to support and buy into the strategy you present to them, but you don’t want them to actually define that strategy.

How to Engage With Your CRO

Make every moment with your CRO count. As a CEO, time with your executives is vital.

Recapping Navigating Choppy Waters: The VC Perspective

Panelists agreed, companies should continue growing and looking ahead, prioritizing thoughtful, data-based decision making.

Signs Your Chief Revenue Officer Isn’t Scaling

Check to make sure your CRO is scaling and growing as much as your company.

What Does Great Look Like in a Chief Revenue Officer?

Over the two-plus decades of working closely with CROs I figured out what “great” looks like and I’ve found that there are five things that great CROs do

Startup Boards, the book, and also why they matter more than ever these days

We’ve done a lot of work around startup boards at Bolster the past couple of years, including working with over 30 CEOs to help them hire amazing new independent board members.

Women Are (Slowly) Gaining Board Seats

Over the past several years, there has been a lot of public attention surrounding board diversity

A CEO’s Guide to Seeking Advice & Mentorship

One of the most common questions we’re asked at Bolster is how to help a CEO find a mentor or advisor

Should You Go Fractional at Work?

6 questions to ask yourself before making the switch to an independent career

7 Habits of Highly Effective Boards

Creating strong boards can help propel a board forward. Weak and ineffective boards hold a company back.

How to Remove Your Full-Time Hiring Hat to Hire An Interim or Project-Based Executive

Hiring an Interim leader can be a great solution when you have an executive leader leave your organization unexpectedly.

When to Hire your First Chief Revenue Officer

In most startups, the founder is the first salesperson and while it may be difficult to let that go you’ll eventually scale, add sales reps, or maybe some form of a Sales Manager once there are more than a couple of reps.

How to Think About Employee Retention in an Economy Where Your Execs Just Want a Change

To better understand the impact of the Great Resignation on C-level executives in the United States, we analyzed the profiles of 5,000+ Bolster members.

What is a Fractional Executive

One of our Bolster members, Connie Kwan, who runs a popular newsletter Product Maestro, wrote an excellent article last week for her audience about how to work on your elevator pitch when kicking off a fractional career

4 Easy Ways for Any CEO to Choose a Mentor

How to frame your thinking about choosing a mentor whether it’s for business or personal reasons.

Joining the Fractional Executive Movement

For the past six weeks, I’ve been quietly piloting the next chapter in my career that of the fractional executive

Signs Your CFO isn't Scaling

While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO

Welcome to Bolster Prime

If you are a CEO who loves to learn, believes that you can learn from someone who has “been there, done that” and wants to not just grow but scale your startup so that you can drive value further, faster, check out Bolster Prime.

The Roots of Bolster Prime and Bolster Ventures

We are announcing the launch of a new program called Bolster Prime, and a new venture capital fund called Bolster Ventures, to empower the innovation economy. The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster.

Bolster Launches Bolster Prime and Bolster Ventures to Drive Success in High Growth Early Stage Companies

Bolster, the marketplace for on-demand executive talent, is excited to announce the launch of Bolster Prime, an 18-month mentoring program, and Bolster Ventures, an early-stage venture fund for Bolster Prime customers.

How to Improve Your Executive Brand Online to Land the Exec and Board Roles You Want

Is the state of your brand online designed to help you achieve your next professional goal? Most don’t know the answer to this question because they don’t google themselves like they google others. Read on to tap into the critical skills today’s execs need to take control of their online presence.

Bolster Raises $11M Series B Financing to Harness the Future of Work Through On-Demand Executive Talent

Bolster, the marketplace for on-demand executive talent, announced today its Series B financing of $11 million to harness the forces driving the future of work for executives and venture-backed startups.

Bolster Your Profile for 2022

The new year is a great time to take control of your personal brand across all online channels, including your Bolster profile, and this post will get you started. It also gives you access to a special workshop to teach you how to develop a powerful executive presence online.

Getting the Help you Need in 2022 - Faster

Speeding up the time to hire can have positive impacts for you, your organization, and the candidate. We offer some tips to help make the hiring process more effective.

What Does “Great” Look Like in a CFO?

A great CFO will spend time learning and steeping themselves in the substance of the business.

When is it Time to Hire Your First Chief Financial Officer

Depending on the complexity of your business you might be able to hold off on hiring a full-time CFO, but if you have any of these signs then it’s time to start thinking about bringing someone on board

New Series: When and How to Hire Each CXO

This series is intended for any C-level executive or board member involved with startups.

How to Engage with Your CFO

As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of work and non-work settings.

Why the Startup Sales Function Starts With “Whiteboards”

In most startups, one of the founders is the first salesperson — often out of necessity as much as passion. But as startups scale they add sales reps or maybe some form of a Sales Manager once there are more than a couple of reps.