Job Search 2019: How Nancy Pelosi and Remote Work Saved Me

This is my story of how a serial entrepreneur for over 30 years turned 55-year-old stay-at-home mother of a toddler, found her way back to a Silicon Valley startup

Photo by Hello I'm Nik 🇬🇧 on Unsplash

My silicon valley startup experience began in 1986, and after a long and circuitous career made up of a handful of ventures; in 2004 I found myself co-founding a company that became known as one of the “darlings of the valley”. 12 years later, for reasons I discuss in an article published in 2016, this same “darling” was quoted as “one of the worst unicorn failures in silicon valley history.”

Now, three years after the end of that amazing yet heartbreaking journey, I feel nothing but gratitude for all that has happened since.

During these past 3 years, I married the woman of my dreams. We added a baby to our lives and have another on the way. I learned how to be a stay-at-home mom at 52, while also starting a small online toddler clothing company. I supported my older daughter as she transitioned from high school to college. I helped my mom transition to a new home and a new stage in her life. Lastly, I started searching for my next career adventure, a new job.

There were many challenges in my life these past 3 years but the hardest part of all was the job search.

Let me start by saying that I had not had a resume or even had a formal interview for a job for 35 years. Since I was 20 years old, I twisted and turned through starting one company after another. I had been part of bootstrapped teams that saw immense successes and fantastic failures. It always felt like doors opened, doors closed, and I walked through them as if it had all been planned with such precision, one experience building on the next.

Until now …

The Beginning: Job Search 2019

I hired a babysitter in early March to watch my 2-year-old baby, Bailey, for 2 days per week. Being able to give my attention to anything other than my daughter for longer than her nap times was something I hadn’t done in a while. The idea was that having a babysitter for 2 full 8 hour days would allow me to actually laser focus on one task for an extended number of hours — the all-important task of getting a job.

On that first day, I said goodbye to Bailey with tears, but also a sense of confidence, commitment, and adventure. I knew that staying at home during this process was not going to allow me to fully focus on the task at hand. So, I commuted from Berkeley to San Francisco to work at an all women's co-working space, The Wing. The Wing gave me a community of women to connect with, which was exactly what I needed for this project.

My Trusted Friend and Good Luck Charm

I fired up my trusty 5+ year old computer, sat at one of the tables with a fresh cup of coffee and started to type my goals and timeline:

  1. Find a position with a team to work with that aligns with my values
  2. Find a company that I can stand behind and am proud to be a part of
  3. Start to look for Advisory and Board positions in parallel to finding a job
  4. Do the above before Bailey’s first day of preschool, September 3, 2019

There were so many questions whirling around in my head as I sat there staring at my computer screen and listening to the buzz of all the women's voices working around me.

  • How do I approach this?
  • What are the key metrics in a company that I need to focus on?
  • What stage of a company do I want to step into?
  • What type of roles do I look at?
  • What size of an organization will I thrive at and have the biggest impact on?
  • How far am I willing to commute?
  • What externally stated values matter most to me?
  • Does it need to be a mission-driven company?
  • Should I also be looking at non-profits that are aligned with my interests?

I looked at my list of questions and wondered if I was overthinking this, or if I should even be asking these questions. The simple fact was, I needed a job. Shouldn’t I just start looking at jobs related to my skillset? My privilege of having space to even consider my list of questions made me feel a strange sense of guilt.

Early in this process, I spoke to a colleague and friend who had been one of our strategic vendors at my previous company. I shared the journey I was embarking on of finding the next venture to become a part of. During this conversation, they asked me, “What exactly are you looking for? You have a breadth and depth of experience in many areas; you need to be clear on what it is you are seeking so that your conversations clearly state the strengths that you want to focus on utilizing in your next position.” I realized that I wasn’t sure how to answer that question yet. I had always been described as an executive-level generalist, the fixer that was brought in to make sense of chaos when others couldn’t. So, my first task was to start to answer that all-important question: What exactly am I looking for in a job?

I began my research with a few basic searches, “women CEO tech company” and “women-founded company Bay Area”. These results brought up some great articles and lists to start digging into. Between Business Insider and Forbes lists, I was able to refine companies to start looking at. My spreadsheet started to come together:

Job Search Research: the rows got longer and longer but I was able to really track all of the data easily and reference it later for cover letter and resume creation

Next, I needed to comb through companies with a local presence, within a 10–15 mile radius of my home. Having a toddler really forced me to prioritize what was important and internalize the criticality of working close to home. Remote work for executives hasn’t really matured yet, so I knew that I was going to need to take a traditional approach and be willing to drive into the office most days. Fortunately, I live near San Francisco, so it allowed me to cast a wide net. I spent weeks researching 100+ companies that met my criteria. I started to get clarity on what I wanted.

My sources for researching if a company was a match for me included:

  • Crunchbase
  • Owler
  • LinkedIn
  • S-1 Filings
  • Articles
  • Podcasts and video interviews of the founders

I narrowed my list down to 50 companies that I was interested in and started the next step of searching for openings within those companies. As I read through job descriptions, it was becoming clear to me that running operations, program management or human resources were areas that most matched my experience. My previous experience was primarily in adtech, but I now believed that the industry mattered less than the actual role I would play in the organization.

My primary places to look for job postings were:

  • LinkedIn — due to the network I had curated on LI over the past 10+ years, in addition to job postings, I also saw articles in my feed that were significant launching pads for finding additional companies to consider.
  • ExecThread — This platform is a great resource for any executive looking for jobs not publically listed anywhere and only available through recruiters.
  • AngelList — one of a few lists where VC-backed startups are posting early job needs.

I was able to source jobs at my target companies plus other similar companies. I was pleasantly surprised to see how well LinkedIn started to source appropriate jobs for me as I started saving my search criteria. I was soon able to find enough positions that it was time to move on to the next step: applying for jobs. I started from the top of the list to research each company and understand everything I could about them. I continued building out my spreadsheet of information to include: team, culture, financials, open positions, current corporate structure, funding amount, funding rounds, interviews, sales decks, and Podcasts.

All of this gathered information gave me a solid foundation on which I could start taking action to apply for jobs. I crafted my cover letters based on the specific criteria required of each job, tweaked my resume accordingly, and started sending off my first few submissions. I knew it was going to be a numbers game, but I was completely unprepared for how many applications and how long it was going to take.

The Middle: Deep into meetings, networking, self-reflection and interviewing

Photo by Jen Theodore on Unsplash

While continuing to search, submit resumes and wait for any sign of life related to a submission I had made, I started to dust off my contact list and began setting up lunch dates, coffee meetings and phone calls. It had been 2.5 years since I had reached out to many of these people. Even though I believed that the best way to find a job was within my own network, I was nervous to call some of them because I wasn’t used to asking anyone for help. I had always seen myself as the fixer that people came to; it had never been reversed. My fear of reaching out to others surprised me. My social media contact lists were healthy, my phone and email contacts were long, but I couldn’t get myself to actually reach out to more than a handful of the people I knew. I realized that this was new territory for me. Not only was I uncomfortable asking anyone to help for the past 2 years, I had mostly been talking to people about diapers, toddler firsts, nap time and potty training. Now I had to have career/industry-related conversations again. This mental shift was going to take some work.

While trying to muster up the courage to reach out to people, I attended an event at The Wing where Speaker of the House Nancy Pelosi was going to speak to a room full of hundreds of women. The event reminded me of a scaled-down version of The Women’s Conference that Maria Shriver created when she was the First Lady of California. The energy was electric. The room was packed, but I found an empty seat. It was soon to be standing room only. About 30 minutes before the event was about to start, a woman sat next to me, pulled out her computer and started typing furiously. I wondered if she was a journalist as she was passionately focused on what she was doing and it felt like it was in preparation for this event. I decided to introduce myself and asked about her work. We spent the next half hour getting to know a little bit about each other and not surprisingly realized we were both in the advertising industry. We exchanged contact info and agreed to connect over coffee soon. I followed up with her the next day and a coffee meetup was scheduled for a few weeks out. I continued to meet interesting women at The Wing and started to appreciate how nice it was to work in a space where women were the majority.

I was now a few months into the job search and I hadn’t yet got that first interview. Doubt started to creep in:

  • What was I doing wrong?
  • Was my 35 years of experience no longer relevant now that I had been out of the workforce for over 2 years?
  • Were the accomplishments of my career not seen as worthy of the level of positions that I was applying for?
  • Was I too much of a generalist for employers to trust that my depth of experience in multiple areas of business was valid?
  • Was my age and/or being a woman a factor in why people weren’t reaching out?

Putting myself out there and not getting any responses forced me to face my fears around rejection, to be open to new possibilities, to stay in the moment even when uncomfortable, and to keep stepping into the unknown, even when my confidence was wavering.

During this period, I was visiting with my Dad’s sister, my Aunt Kathy, and sharing my discouragement and doubt in how my dad had taught me to navigate life. He told me to write down my goals and timelines, and do the legwork required to accomplish the goals — this was the easy part of his training. The next set of his core teachings were more challenging:

  • Trust in the path in all of its many directions even when it doesn’t always make sense
  • Always be open to serendipitous events
  • Never allow doubt to consume me
  • Always keep in check my thoughts and attitudes to remain positive and focused

My Aunt smiled at me, with the same fiery blue eyes as my father, and said, “Dianna, now more than ever you must trust those teachings. They have got you to this point in your life that you treasure so much.”

Her words of wisdom reassured me. I continued to connect with more people and was given a couple of tactical tips:

  • The importance of matching keywords in my resume and LinkedIn profile to the jobs that I was applying for. I hadn’t realized how the *exact* phrases I was or was not using were related to how well I ranked on the job description page and the search results that the recruiters were viewing.
  • Keep my resume and online profile focused on the types of jobs I was looking for. This was difficult because I was applying for Operations, Human Resources and Product Management roles. I had to be sure that I didn’t appear to be a “Jane of all trades” even though that was exactly what I was.

After many months of submitting applications for jobs, meeting with friends and scouring through my network to find companies that met my requirements, I was still not getting any results. I had submitted many highly curated cover letters and resumes to CEOs, CxOs, recruiters, friends who could refer me, and even a few direct cold submissions through career sites. Nothing was getting me an interview. I wasn’t getting looked at, called or even emailed a rejection letter. The self-doubt continued, even though my deeper trust in knowing that I had to walk this path to get to where I needed to go had not yet wavered.

One great thing had occurred during this period. Rae, the woman I had met at the Nancy Pelosi event at The Wing a month earlier, had asked me to be an advisor to her company. I allowed my instinct to drive the decision and with very little hesitation I accepted the offer. I had also started discussions with a few others about an advisory or board seat and seemed to now be making slow progress towards that. Having these relationships and possibilities gave me some validation and lifted my spirits as I continued down this path of finding a job. I kept telling myself that if only I could get in front of people for an interview, I would be able to show them all that I could offer. That process would allow me to start to assess and critique how my presence, communication, and experience resonated with those that I interviewed with. Because I hadn’t been successful in getting in front of anyone yet, I decided to change my approach to this:

By doing this, I was finally able to get my first break. I found a company with a job that perfectly matched the criteria I had set for myself and a very close contact could get my resume in front of the executive team member hiring for the position. This company became my first full interview cycle. I met with a few C-levels, along with ten additional team members over three sets of interviews, in a one month period. I really got into the groove of understanding what about my presentation style clicked and what did not, with all the different levels of people in an organization. I had never done a formal interview in my 35-year career prior to this. It was a great learning experience and I am grateful for it. Going through this interview cycle gave me the confidence that I needed to pick up the phone and really start connecting with everyone and anyone that I had ever helped or supported.

  • I began researching recruiters to meet with to see about early-stage startups that may not have job postings.
  • I met with co-founders from my previous companies. One of those meetings allowed me the opportunity to interview with their company CEO for a potential position that had not yet been created.
  • I called VCs that had funded my previous companies to see if they had any portfolio companies that I might be able to fit into.
  • If there was a startup that I found intriguing I reached out to the founder and asked if we could have coffee. One of those meetings turned into a wonderful relationship that I believe will continue long after I settle into my next venture.
  • I called senior contacts of companies that I supported in my previous company. One of those connections ended up helping me find my second advisory position with her current company.

During this phase, I went through an additional 2 rounds of interviews with a company that my previous co-founder was working at, received 2 rejection letters from places that I was referred to, and did 1 phone interview with a company for which all of my keywords stated I was a 90% match. Still no job offers.

All of this face time with potential employers led to rejections but surprisingly motivated me, because I could sense that I was easily able to connect with people in various industries. The jobs were not yet right, but what I was finding were injections of enthusiasm, energy, and connections that continued to solidify my vision of what I wanted to do next. I had also started comparing the companies that I was interviewing with to the company for which I was now an Advisor. I was experiencing so much fun, creativity, joy, and fulfillment working with this team that I didn’t want to settle for anything less than that in my next job.

The End: 40+ job submissions, 3 company interview cycles, 4 rejections, and 100’s of connections

It was now September 3rd, the day by which I wanted to be employed. My wife Clare, our daughter Bailey and I had just returned from our summer vacation and were starting to get ready for our new daughter’s birth, which was just 4 months away.

Bailey was starting her first day of pre-school today, which was a major milestone for us as a family. Clare and I dropped Bailey off at school and shed a few tears as we walked to our car to go to San Francisco. As we drove in, both of us reflecting on the past 2 1/2 years of raising Bailey, I reminded myself of how blessed I was to be able to have experienced staying at home for the first time, in my 50s, to raise our child.

I dropped Clare off at work and headed to The Wing to continue my job search. As I walked up a flight of stairs I was again reminded that today was my deadline to have secured a job. I had missed my goal, something I never took lightly in my career. I was feeling a bit down when I entered The Wing but was greeted with a kind smile at the reception desk. I chatted with the woman at the desk for a few minutes and then was preparing to go find a seat and dive back into the job search when I heard a voice from across the room calling my name. Rae, the woman I met at Nancy Pelosi’s talk, the founder of one of the companies I was advising, came running over to me and gave me a warm hug. We hadn’t seen each other in 2 weeks and were both happy to reconnect. We caught up while chatting in the hallway and as things were winding down she asked me how my job search was going. I shared my status along with the experience of a phone interview that I had the previous week. I laughed about how every position I was looking at now was being compared against her company. She then gave me a big smile and said, “About that … Lee (her co-founder) and I spoke while you were gone and we wanted to ask you what it would take for you to stop looking and instead come work with us at Sandy?”

The next week I started my new job as the Chief Operating Officer of Work Sandy (Sandy) — the company I had been advising and that was my benchmark for all that I was looking for in my next venture.

This journey has not only humbled me but has also reminded me to trust in divine timing — another core part of my father’s teachings. The conversation with my Aunt in the middle of this journey kept me confident in the training he had given me prior to him leaving this physical world 20 years ago. My Aunt had also shared, “This trust in the process will continue to lead you to a place that is exactly where you need to be at the timing that is best for you”. She was right.

Two of my Loves — Bailey and Jordan

About Sandy — Sandy is a next-generation, elite freelance talent network, and service platform, built to connect advertising agencies with on-demand, elastic teams of diverse top-tier creative talent . My job is to be a key contributor in the creation of our marketplace with diversity, equity and inclusion at its core, which is both close to my heart and critical for business success in the modern era. Our entire team is spread across the globe, and we fundamentally believe that the most successful companies of the future will rely heavily on remote and freelance talent to move their businesses forward. The days of 9–5, brick-and-mortar office life are dwindling, and we intend to be a critical player in ensuring that this reality will improve the quality of work (and life!) for our customers and talent alike.

A serial entrepreneur and co-founder of venture-backed Mode Media. She has a deep passion for startups, equality and inclusion, women-led ventures, and coffee.

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