Showing up as Your Unique Self: Emma Holland’s Job Search Success Story

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In this job search success story, Emma Holland, the National Community and Volunteer Manager at StartOut, shares how she sought support and embraced her authentic self during her job search.

What do you do for a career? Who do you work for?

I am a community professional, which means I support a lot of an organization’s efforts to maintain and sustain satisfaction/retention with clientele, strategic partners, sponsors, and public brand trust. Community Managers engage audiences on a variety of outlets, including online forums, online events, Slack, small in-person groups, and more. Uniquely for StartOut, I also manage our volunteers via industry programming boards while directing community strategy for org growth, scale, and member retention.

I currently work for StartOut, the national nonprofit working to increase the number, diversity, and impact of LGBTQ+ founders. Our small team works to amplify our founders’ stories to ultimately drive the economic empowerment of our community. Please visit us:

How long did it take you to find this job?

Somewhere between three and four months. I began applying while I was still a full-time employee for another organization. 

How did you find your job? What resources did you use? What tool or tactic helped the most?

I was eager to find a new role. After working in a space that supported career switching for adult learners, I decided to put some of that strategy to use for myself. I applied for 4-6 roles a day, Monday through Friday, for three-ish months. I updated my resume formatting after researching applicant tracking systems. I created a new personal website. I sent messages to professionals on LinkedIn working in roles similar to those in which I was applying. I conducted at least one informational interview per week. I had a notification for LinkedIn to email me about remote roles posted with titles similar to mine within 24 hours, knowing I needed to catch them early.

I used LinkedIn, Idealist, Mac’s List, and (mostly) Slack to find opportunities and speak with hiring managers. Our local icon, Rick Turoczy, maintains an incredibly robust Slack group for the Portland Startup community, and the Out in Tech team has a vibrant group for LGBTQ+ folks in the job-search, providing career and resume advice. A dear friend and former colleague is a career coach based in Chicago. She gave me a ton of advice on my materials, my process, and how to negotiate. If you’re financially able, working with a coach can really be a game-changer!

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What was the most difficult part of your job search? How did you overcome this challenge?

At one point, after months of rejection, I had a verbal offer from a Portland-founded finance company. My new manager had reached out, people were connecting with me on LinkedIn, and the recruiter told me at the end of the week they would send over the written offer. The very next week, only days later from my offer, news broke that their parent company intended to shut down all operations of this company by the end of the year. An hour after I caught the headline, I received an email letting me know they would not be able to move forward with my offer and had stopped hiring for their Portland operations. I was shocked and disappointed, having already canceled some of my following interviews – but thankfully held onto one that felt too good to be true. The following day, I had my final interview with StartOut’s Executive Director.

I don’t think I did 100% successfully overcome all the things constant rejection had me think about myself or my abilities. My current manager tells me regularly that my work is tremendous, shows me the data, and she’s telling me regularly that I should be proud (and not doubt myself). But there is some gaslighting that happens throughout a job-seeking process. Getting ghosted by a recruiter is terrible and makes you wonder if you’re actually worth someone’s time. Getting told after five rounds of interviews that they went with another candidate, on multiple occasions, really makes you wonder, “why am I not good enough?” After a couple of months, I decided to reach out to my community to share that I was struggling and the Program Director for Out in Tech became such a champion for me, offering intros and singing my praises. It was awesome knowing someone believed in me, and I felt stronger by asking for help in a trusted space. 

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What is the single best piece of advice you would offer other job-seekers?

Most of these systems are not designed for all the uniqueness you bring to the table, so don’t take everything to heart or you may doubt your worth. Also, some job postings list “requirements” but should be branded as “guidelines” – if you think you only have 70% of the experience they say they require, apply anyway! My main experience was in eLearning and EdTech, but I was interviewing with healthcare, finance, nonprofits, marketing agencies, and production companies. Practical moment: Make sure your resume shows your impact in your roles, with key data figures like “improved retention of clientele by __% in 6 months.” Also, look at the skills the listing is hiring for, then include the applicable ones (as comma-separated-values, not bullet points) in your resume!  

Why do you love your job?

I am still amazed that as a nonprofit, my organization was willing to pay me more than the giant corporation I was working for, with better healthcare, all while supporting me being fully myself in a public role. My manager is incredible as a coach and collaborator. The team is intentionally diverse (this is the first org I’ve ever worked for with transgender representation on the Board of Directors) and our overall team focus is consistent: “what is our impact?” We are consistently centering on the experiences of our members and clientele. I’m trusted with autonomy and consistently have collaborators all across the organization supporting my work while helping me refine our strategy. I feel aligned with the mission and encouraged to be my authentic self – and I’m encouraged to take the time away I need to care for myself without guilt. It’s pretty remarkable how much better I sleep!

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Everyone’s job search story is different, but each individual story can inspire and empower others who are on their own unique path. We love to hear how our readers have found rewarding careers in Portland, and we want to share these stories with you to inspire you in your job search and to help us all better understand the local job market!