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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 recruiting team what executive hiring trends they expect to see in 2024.

3 Myths CEOs Believe About Hiring Executives

Executive hiring is a critical part of your leadership strategy, but common misconceptions can lead to costly mistakes.

Understanding CXO Archetypes: Chief Marketing Officer

We’re looking at common CMO archetypes, including what makes each unique, how to identify them, and how to know which one to hire.

Meet the Recruiter: Martha Kaser

We sat down with Martha, a Bolster recruiter, to discuss how she thinks about search.

How To Retain Top Executive Talent

Guests from The Daily Bolster share advice to help you retain top talent once you find it.

How Top Companies Are Approaching Executive Search for Success

The best results occur when your hiring team is prepared, clear on the role, open about expectations, and committed to the process.

Avoiding the Trap of “The Big Hire”

When CEOs start looking for “the big hire” to fix the business, the chance of an unsuccessful placement increases significantly.

Meet the Recruiter: Sarah Auten

We sat down with Sarah, a Bolster recruiter, to discuss how she thinks about search.

Book Recommendations from The Daily Bolster

We’ve compiled a list of books discussed on the podcast.

Deep Dive with Seth Godin

Renowned marketer, author, and thought leader Seth Godin recently joined us for our 200th episode of The Daily Bolster.

7 Questions You Should Ask Executive Candidates

Guests from The Daily Bolster share the questions they ask in executive interviews—and what they’re looking for in response.

3 Reasons Why You Shouldn’t DIY Your Executive Search

Running an executive search on your own might be a tempting option, but there are a few pitfalls CEOs should keep in mind.

Meet the Recruiter: Patti Dorsey

We sat down with Patti, a Bolster recruiter, to discuss how she thinks about search.

5 Signs Your Executive Search Will Fail

Bolster’s executive recruiters share the early signs of an unsuccessful search.

Deep Dive with Carolyn Everson

Successful executives like Carolyn Everson have valuable advice for leaders, which is why we dive into their career journeys on The Daily Bolster.

3 Tips For A Successful Executive Interview Process

Bolster recruiters share tips for interviewing executives, from understanding candidate expectations to the right questions to ask.

Getting Started with an Executive Search Partner

We asked our team of executive recruiters what companies should expect when starting an executive search with Bolster.

The Daily Bolster on Building A Great Board

Guests from The Daily Bolster talk about building, leading, and cultivating successful boards.

Meet the Recruiter: Patrick Corcoran

We sat down with Patrick, a Bolster recruiter, to discuss how he thinks about search.

When is Fractional Enough?

It’s possible to benefit from the expertise of an executive without the commitment of making a full-time hire.

Insights on Coaching and Professional Growth from The Daily Bolster

Guests from The Daily Bolster talk about the importance of professional growth, the role of mentorship, and more.

Why is executive search broken?

We asked our team of executive recruiters to share their perspective on what’s wrong with traditional executive search.

The Daily Bolster: How to Interview Executives

Guests from The Daily Bolster give advice on how to interview and hire the right leaders.

Meet the Recruiter: Christine Berg

We sat down with Christine, a Bolster recruiter, to discuss how she thinks about search.

What Type of Leader Do You Need?

Flexible work types offer solutions tailored to your needs—but how do you find the right fit?

Laying the Foundation of a Great Partnership

Strategic business partnerships can be transformational—but how do you build successful ones?

How To Engage With Your CBDO

Building trust and clarity takes time, so it’s important to engage with your CBDO regularly, even when you’re not actively working on a deal together.

Do You Have the Right People on Your Board?

As a CEO, having the right people on your board should always be among your top priorities.

Tune in to Season 3!

The Daily Bolster podcast is back with Season 3! We're recapping some of our favorite moments from the first week of episodes.

Signs Your CBDO Isn’t Scaling

How do you know if your Chief Business Development Officer is scaling? Check out these signs to watch out for.

Bolster’s Year in Review

2023 was a year of growth and progress for Bolster. We added new members to our team, supported more clients in new ways, and continued evolving our platform's capabilities.

3 Expert Tips for Effective Decision Making as an Executive

Practical advice for decision makers. Use these tips to alleviate stress and to make decisions you feel confident in for the long run.

What Does Great Look Like in a Chief Business Development Officer?

Finding a great CBDO is tricky, but looking for these characteristics will help you find the right leader.

10 Top Clips from Our First 100 Episodes

To celebrate 100 episodes of The Daily Bolster, we’re sharing some of our listeners’ top clips.

Keeping Diversity in Mind with Full-Time Hiring

If you don’t take steps to ensure your organization is inclusive, it won’t magically become that way.

Bolster Expands Services to Include Leadership Consulting for High-Growth Companies

Leading Executive Search Platform Bolster Offers Enhanced Executive Evaluation and Development Solutions

Navigating a Non-Linear Career: Insights from a B2B Tech Marketing Leader

During Season 1 of The Daily Bolster, Matt and Sarah Brown shared insights on the nuances of non-linear career progression, strategies for transitioning between roles, and the art of leaving a company gracefully.

Onboarding New Executives Remotely

With remote work here to stay in some capacity, it’s important to create an effective onboarding process for remote executives.

When to Hire Your First Chief Business Development Officer

Whether or not you need a CBDO depends on many factors, but these signs can help you evaluate what’s best for your team.

How To Identify Potential Leadership Talent Early

We asked experts from our talent search team for their top tips for discovering potential leadership talent.

The Daily Bolster is Back!

We’re sharing a few of our favorite moments from the first week of Season 2.

How To Engage With The Chief People Officer

You won’t always have a ton of time to engage with the Chief People Officer, so you should know how to capitalize on your interactions with these executives.

Webinar Recap: Hiring with Precision

Scaling your leadership team is a vital part of scaling your company. Now is a great time to think about your hiring strategy.

5 Unexpected Interview Questions to Ask Executive Candidates

Interviewing is a mix of art and science. We’ve gathered five interview questions that can help you get to the heart of a candidate’s potential.

The Daily Bolster: Recapping our Deep Dive with Brad Feld

We can learn a lot about success and growth just by looking at the history of entrepreneurship. Brad Feld and Matt Blumberg discuss what’s changed in the startup world.

Signs Your Chief People Officer Isn’t Scaling

If you have a Chief People Officer who is transactional, doesn’t speak up, and has morale or turnover issues within their own team, you’ll need to address it quickly.

Bolster Expands Services with Full-Time Executive Search Offerings

Leading Executive Talent Marketplace Bolster Adds Full-Time Search to Its Portfolio of Offerings

What Does Great Look Like in a Chief People Officer?

A great Chief People Officer is strategic, courageous, and financially astute. They know they’re the role model for the company; their behavior sets the tone.

The Daily Bolster: Insights on Executive Hiring

Guests from The Daily Bolster give advice on executive hiring: how to find a leader who can do the job, fit into your organization, and help it grow

When to Hire Your First Chief People Officer

As a startup, it’s easy to focus on the tangible, tactical operations of the People team, but if you want to scale, you’ll need someone in your organization who cares deeply about your values.

Startup Highlight: Looking Glass

We interview a startup founder: an outside-the-box idea, a love of learning, and an exciting vision for the future.

Why Hiring Executives is Challenging for Startups

Recruiting top-tier executive talent is a challenge. For startups, hiring the best talent comes with a unique set of obstacles.

The Daily Bolster: On Being an Entrepreneur

We’re sharing a selection of podcast episodes specifically curated to help you succeed as an entrepreneur.

4 Tips for a Successful Executive Search

A new leader can transform your team. Make sure you hire the right person for the job.

How to Engage With The Chief Privacy Officer

When things spin out of control, you need to be able to trust your Chief Privacy Officer, hit the ground running, and help get everything sorted out.

Insider Information: Directly From VCs

Get inside the heads of prominent VCs: standout pitches, common founder mistakes, hearing the word “no,” and more.

Signs Your Chief Privacy Officer Isn’t Scaling

Your CPO needs to be able to engage the entire company, be thinking strategically about the business, and have short- and long-term plans in place for contingencies and foreseeable roadblocks.

Q&A: Reimagining the Board Meeting

The all-star panelists from our recent webinar answer questions about why the board meeting is broken.

What Does Great Look Like in a Chief Privacy Officer?

Don’t wait until you have a data breach to hire a great Chief Privacy Officer. By the time you have an urgent need, it will be too late.

How Fractional Executives Drive Startup Growth

Fractional executives offer a powerful solution for startups looking to drive growth and overcome unique challenges.

Ethics in the Age of AI: Webinar Recap

Our guests break down how generative AI can be leveraged across key industries, what it can do well, and the potential pitfalls.

When to Hire a Chief Privacy Officer

Some startups don’t have any support in the Privacy role at all, but given the importance of privacy and security issues today, that’s a mistake.

The Daily Bolster: Week One Recap

We’re recapping the podcast highlights from Week One, plus giving a little sneak peek into what we have in store for next week.

Grow or Die

You can't possibly be successful in today's world if you're not learning, if you don't have a growth mentality. You’re never the smartest person in the room. The minute you’re convinced that you are… you're screwed.

Announcing The Daily Bolster

We’re thrilled to announce The Daily Bolster—a quick-hitting podcast for startup leaders scaling their businesses.

How To Engage With The CCO

One of the most productive ways to engage with your CCO is offsite and with customers. This builds a clear understanding of your customer base and their challenges.

The Quest for Diversity in Tech Leadership Is Stalling. Here’s Why.

If they don't do the work, tech CEOs will continue to bemoan the lack of diversity in their leadership ranks and miss out on the benefits of diverse leadership, while not taking ownership for those efforts stalling.

Signs Your CCO Isn’t Scaling

Your CCO should be looking far enough ahead to begin thinking about upcoming challenges and working to develop solutions that scale with your organization.

5 Things Successful Founder Operators Do Differently

None of these practices is the path of least resistance, but there's something in them that leads to the competitive edge, the informed intuition, the vision, and the ability to motivate people that are common in successful founders.

What Does Great Look Like in a Chief Customer Officer?

The great CCOs all have the same traits: they are advocates for the customer, have a mix of quantitative and qualitative skills, and are passionate about processes that create a seamless, functioning team.

Recapping Navigating Choppy Waters: Equity Market Temperature Check

Investors are looking for viable businesses that have traction and product market fit—there’s less focus on unproven but good ideas, and more focus on paying customers and a clear path to profitability. The current market is less about FOMO and more about fundamentals.

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 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.