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Ascend Panel Recap: How To Be An On-Demand Executive -- Stories From Real Bolster Members

Last week Bolster’s partner, Ascend, hosted a panel discussion about the path to on-demand executive work. We had a glitch with the recording, but wanted to make sure that even if you missed the live event, you could benefit from the conversation’s key takeaways. Enjoy!

We started with this poll to get a gauge on the audience’s thoughts on this topic:

Answer: All of the above!

Meet our Panelists – all are successfully placed Bolster members:

  • Connie Kwan is a fractional Chief Product Officer
  • Linda Choong is a fractional CEO Advisor on Strategy, Product and Operations
  • Caroline Kim Oh is a fractional Executive and Leadership Coach
  • Bolster Co-Founders, Cathy Hawley and Ken Takahashi
  • Michelle Nasir, Chief Talent Officer at Arsenal Capital Partners & Ascend Moderator

First, moderator Michelle asked Bolster Co-Founders, Cathy and Ken, to set the stage for the conversation with a few slides: What is on-demand work, what is Bolster and who do we serve?

Bolster helps companies scale their executive teams and boards.

  • Members are experienced C-level talent.

  • Clients are CEOs of startups and scaleups.

    How CEOs determine when to hire an on-demand exec and what type they need:

    Why Execs, Clients and others see value in a marketplace like Bolster:


    The beauty of on-demand executive work is that it doesn’t have to be what it used to be called: consulting. Today there is more than one way to have a big impact on an organization than being a traditional full time executive, and Bolster facilitates that for members and clients.

    Members are able to work on things they are most passionate about, on their terms. And Clients get value because they can tap into a network of career-tested executives for exactly what the business needs, and plug them in at the highest levels for the greatest return.

    Who applies for these roles and how do you typically matchmake between the person looking for the on-demand exec and the member in the network?

    Bolster doesn’t have an application process per se. Members create a free Bolster profile and some of the things we capture on the intake process are skills and super powers (the 3 things you are the best at, the things that you really shine in) and ‘sweet spot’ (what is the area where you add the most value). And then when a client comes to us, we do a bit of work to help them figure out what is most important to them, and then the database algorithm works to connect those two. The system suggests people who look most qualified, allows them to connect and explore if there is a fit.

    Can you talk about what these roles look like in high growth startups, VC and PE?

    A lot of startup and scaleup organizations are growing at 50/60/70% year over year and their next stage is coming up faster than they can plan for it. It helps to bring on external leaders who’ve been two or three stages ahead to coach and mentor that functional leader rather than displacing them. If you think about the lifecycle of a portfolio company it’s about getting ready to scale, getting ready for growth, adding new capabilities, so there is a natural need for on-demand specialized talent.

    What gets in the way of people taking on these roles?

    There are historically some road blocks, both on the member (talent) side and the company (client) side. Execs can be scared of going out of the safety of a full time role, so at Bolster we are trying to help some of those barriers to make it easy so they can just focus on the work that they love. Our billing and collections service is a good example of this.

    On the company side, these roles have always existed, but only on the periphery and usually in certain functional areas such as Finance. We believe that to get the full benefit of this talent, these roles need to be integrated into the structure of the organization’s management team.

    These barriers need to come down for everyone to really embrace this.

    Connie, can you talk to us about the importance of branding as an on-demand exec?

    When I transitioned from full time work to fractional exec work, I approached the problem through storytelling:

    • How do I package up my services as a product?
    • How do I tell the story of that product?
    • How do I get my customers excited about what I’m offering?
    • How do I use the interviews to understand what they need?

    The interview dynamics are flipped as a fractional exec, where CEOs are shopping you, vs when you’re looking for a full time job, you are shopping them. So the challenge is: how do you tell that story of what you are offering in a way that makes it attractive for founders and CEOs to want to work with you? I spent about a year trying different things and figuring out what I wanted my special sauce to be. It doesn’t work to try to be everything to everybody.

    As moderator Michelle noted, this is all about understanding your super powers and how to market them.

    Linda, can you talk a bit about how you fell into on-demand work?

    I always say that I fell into it because that’s how it felt to me…My first client came out of networking after I had been re-orged out of my last role, and this project led to a 6 month engagement.

    I think what most surprised me was how much I loved it. I expected to miss being part of a team, but I realized that you have that ability to recreate that dynamic, even on a project basis. That was really exciting. And since then my clients have been mostly through my existing network, or through Bolster.

    The flexibility afforded me was a big part of me wanting to stay in this on-demand business because I could help my parents who were getting older, but also in my transition period I had made a decision that I wanted to spend more time volunteering for things that are important to me, and this portfolio career really allows for that.

    Caroline, can you speak to the idea of ramping up and ramping down in your career?

    I work with a lot of senior executives and even if they are trying to think about a new role in general outside of their current work, any sort of change is very scary when you have a big job and compensation package. To go for any type of big change, it’s important to have that sense of economic security and psychological safety so that you can take risks. Thinking through your financial situation, or thinking through the network of people who can help you, or a marketplace like Bolster that can help you find work – all of these things are important to open your mind to new ways of working, especially a portfolio career.

    It’s also important to reflect on what your best, most successful self needs to be successful and put a team, resources and boundaries around you to be able to achieve that.

    “Beyonce without help is just a lady who sings and dances well.” ← Caroline won the best quote of the panel!

    Key takeaways:

    • Sounds simple, but thinking through what’s really important to you and re-training your brain (and your calendar) to be structured to support this new way of working.
    • Taking time to do an “offsite” with yourself, the same way you would with your team to check in and make sure you’re on track with your goals and approach to achieving them.
    • It’s critical to understand your super powers and how to market them to CEOs.

    Q&A:

    • What type of projects are you seeing more requests for on-demand execs? → We’re seeing a pretty broad mix of strategy to executional. Still seeing portable roles like fractional CFOs, interim Chief People Officers or someone to help with an RFP or raising the next round, like you might have thought of, but also as demonstrated by this panel a lot of strategic and advisory roles per function to help a functional leader to see steps ahead of where they are. We often see that execs particularly like one or the other and are guided by their sweet spots: either very hands-on work or more high-level advisory, strategy work. We are also filling a lot of board of directors roles.
    • Could the panelists share a bit about their personal experiences with Bolster? →
      • Caroline said: “I really wish that a service like this existed when I was getting started, because getting that sense of safety and a little bit of scaffolding to support me and give me a bit of structure would have helped me out a lot because it was pretty scary.”
      • Connie said: “The client that approached me through Bolster was already primed to have a fractional executive, so the conversation was much easier, the selling cycle was much shorter, and because to them it was a fractional and a part time interim position, they didn’t have to put me through a lot of interviews to say yes. So that was a really smooth experience. So thank you to the Bolster team – really love that you guys are being a part of helping fractional executives find opportunities.”
      • Linda said: “Bolster’s done a really good job of matching me with people who would have been outside of my normal network, but just from a personality, fit and experience perspective, it just worked really well. So even in a situation where the referrals didn’t lead to something, I could have imagined myself working there, so that’s a credit to them and their matching process, which I think is really helpful.”

    We gave away 3 copies of Bolster’s new book “Startup CXO” to 3 people engaged in the chat.

    We encourage you to check out the incredible work that Ascend Leadership is doing to advance the executive inclusion conversation for Pan Asian executives. In fact, they just launched their 10x25 campaign, which Bolster is proud to support, to achieve at least 10% of AAPI directors on Fortune 1000 companies by 2025. Learn more and get involved here.


    We hope you’ll keep in touch. Please subscribe to the Bolster blog to stay informed of new resources and ideas. And if you are curious what’s on our CEO, Matt’s mind, you can subscribe to his personal blog here.

    -Dana Ostomel, June 22, 2021