From Unpaid Intern to $260k as Chief of StaffFeatured

Our Salary Paths series aims to give fellow Elphas a reference point for salary negotiations and encourage more women to talk about compensation. We hope that opening up the conversation will contribute to more pay transparency and equitable pay.

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Across 7 jobs, these were my guiding principles:

  • Never take a pay cut. If I was moving jobs, I would only accept jobs that gave me more than my current salary.
  • I took on diverse roles across multiple industries and tried to not do the same role once. This meant being very junior in many roles - business development, sales, marketing, and operations were all of the different jobs I tried. The goal for me was to find out what I 1. was good at, 2. enjoyed, and later on, 3. would be paid for.
  • I worked part-time during the first two years of my Bachelor’s degree, and full-time for the last two years. This isn’t for everyone, but I needed to survive.

Job 1, B2B Local Healthcare Wearables Startup, Marketing and Sales Intern (Unpaid)

I got this job through a club I was in at university. In this role, I attended some sales calls, designed some product manuals in Adobe Illustrator, and did lead generation. This startup ended up going to YC, so I got lucky. However, remote work wasn’t popular at the time so I was out of a job for the upcoming summer.

Job 2, B2B Local CPG startup, Operations Intern ($1000/month)

This CPG startup shared the same incubator as my previous role, so we were easily connected as they were looking for a summer intern. This startup had a lot of internal problems (underpaying employees, no employment contracts, micromanager CEO), so I was fired in 3 weeks and sent home with $936.70.

Job 3, B2B Small Robotics/Education Business, Camp Counselor (Minimum Wage, $11/hr)

After getting fired during that summer, I was out of a job and desperately needed money. I took two days after being fired to relax. Then, I set a quota for myself to apply for 10 jobs a day. 8 days and 80 applications later, I was called in to do an interview where they hired me on the spot. I taught kids how to use Scratch and make a robot move through educational activities at a camp.

Job 4, B2C Local Fintech Startup, Business Development Intern ($15/hr)

I had networked with this startup at a local startup event during my time at the robotics company, and started volunteering with them near the end of the summer. This was my first real experience with startup culture - 14-hour days, excessive caffeine, and pasta as our main source of food. After a few weeks of volunteering for them, they offered to start paying me well above minimum wage, which was excellent at the time. We entered YC Startup School, where our mentor told us we needed to double our users week over week. Through spamming our product on Facebook groups, and making good landing pages, I scaled the company from 300-100k users in 4 months, and we got into YC.

This was my first real success at a startup, and it invigorated me to want to work for more startups. I was also the first business hire at this startup. I learned a lot about growth, some tools like Mixpanel, Notion, and Airtable.

Job 5, B2B Small Robotics/Education Business again, Marketing Intern ($16/hr)

Again, remote work was not popular, so I was out of a job while the local fintech startup went to YC for the summer. I went back to the robotics business, and, in my own words, I asked to “work in the office”. I learned about Google Analytics, and I helped out each department. I helped sales improve their B2B decks and materials, and I helped engineering narrow down on the metrics to improve their D2C sales on their website. I narrowed down on B2B metrics that were important to a business.

Job 6, B2C Education Company, Human Resources Generalist ($17.50/hr)

I applied to this job through Indeed. The reason I got this role was because I had managed HR for a charity I was with, so they felt I was qualified for an HR role. I managed 5 executives and 20 employees doing payroll, event planning, and other administrative tasks. They had a lot of culture problems, so I ended up leaving.

Job 7, B2B Medtech Startup A, Business Development Intern - Operations Associate - Head of Operations ($45k, then $75k yearly)

I applied to this job on AngelList. The reason I got this role was because I was working on a side project involving reusing medical packaging in hospitals, and my knowledge of hospital bureaucracy convinced the founder to hire me. I banked the most hours at this startup, and I worked from 8am to 8pm every day. We tried six different methods: going to the doctors' offices in person to sell our products like pharma reps, emailing doctors, delivering custom gifts to doctors, offering to buy doctors lunch, cold calling clinics and we finally landed on faxing doctors. It took about 6 months of straight cold calling along with these other items to get our first deal, which was a sizable amount.

After getting our first customer, we needed to do customer support. I had to learn a lot about operations, write SOPS, and talk to patients to see what kind of problems they experienced.

Eventually, we had our sales cycle completed, the first customer, and CX process created, so hiring came next. I found that I was really good and enjoyed hiring and interviewing folks. I started by making job postings and networking with recruiters on Clubhouse, who gave me good advice on what recruiting cycles looked like, recommended tools and shared their recruiting decks with me. We had to hire everyone needed for a Series A, so it was roles like engineering, marketing, sales and more. Eventually, I scaled the company from 7-35 people in a year.

I left this startup abruptly because payroll had stopped and the company was running out of money.

Between Job 7 and Job 8: Finding My Way

As I mentioned at the beginning, I had to work during my schooling. This meant aggressive job hunting when I was out of a job. I was lucky enough that one of my friends who was a YC founder put me on Bookface, which is YC’s internal job board. She endorsed me and helped me come up with a blurb, and this enabled me to network with many other YC founders looking to hire. This led to a chain reaction of founders hearing about me through the grapevine - even non-YC founders. This enabled me to strengthen my connections with my existing network by asking them for advice, but also signal to them that I was available to work and in high demand. I am very grateful for her help.

Job 8, B2B Medtech Startup B, Recruiting Lead (Contract, $65/hr)

I had previously networked with the founder of this startup on LinkedIn, but it didn’t go anywhere. I cold messaged him and asked if he had any roles available, and he did have a recruiting lead role available. I did the same thing I did in Job 7, except I had a budget to advertise roles which was nice. Everyone on the team was great to me, and there was a culture of transparency, respect, and ownership.

I interviewed actively throughout my time at this company even after getting the role, because the contract would come to an end. They offered me a full-time Head of People Role at $95k a year at the end of the contract.

Between Job 8 and 9:

Knowing the contract was ending, I gathered other offers well in advance:

  • The CTO at B2B Medtech Startup A offered me a Head of People Role at $115k/yr at his new company, Gaming Startup, as he had also moved.
  • A B2B Devtool Startup (a vendor we used at B2B Medtech Startup B) attempted to poach me and offered a Head of People Role at $95k a year.
  • Last in the arena was DevSec Tool Startup, which I wasn’t sure wanted me.

I first accepted the offer from Gaming Startup, who at the last minute rescinded my offer. Then, I verbally accepted the offer from B2B Medtech Startup B, and rejected B2B Devtool Startup out of goodwill. However, B2B Medtech Startup B took more than a few days to provide an employment contract to me, and DevSec Tool Startup swooped in. The founders had seen my intro on Bookface and were friends with the YC founder who put me on the job board. They knew I had a lot of other offers, interviewed me, and sent me an employment contract in less than 24 hours, which I accepted. I felt bad verbally accepting the offer from B2B Medtech Startup B and signing DevSec Tool Startup’s contract, but I was honest with the founder about the employment contract being delayed.

Job 9, DevSec Tool Startup, Chief of Staff ($170k base salary + $90k equity, total comp $260k)

I am super happy to be at my current company and have a diverse leadership team, and my roles and responsibilities change every day. Diversity is implemented intentionally at our company: our hiring practices, the insurance companies we pick to provide healthcare to our team, our case studies, everything.

I'm happy to take any questions and I'm grateful to the Elpha team for letting me share my story. Thank you @Josefina!
Love your journey!! Could you share more about how to navigate financial pressure such as big student loans while navigating the current job market as a Masters level international student in the USA? Also for women who may feel too shy to do the intentional networking. Are there other avenues to network remotely or in-person? Thank you so much for sharing your journey in so much detail.
Hi, OP here. Thank you for your kind comments. Unfortunately I went to school outside of the United States, but worked for U.S. based companies as a contractor for job 7. My student debt was not as large and more manageable for me, so there's very little advice I can offer to you there. For networking, I think you have to just put yourself out there despite feeling shy, by any means you can. I felt very shy and still feel shy networking now, but with enough practice and speaking to enough people you'll feel more confident. Also, think of it as an exchange of skills rather than you wanting something from the other person. Put yourself out there, because you can do it!
Greetings from Northern Italy! I find myself back on the job market looking for my next remote job opportunity and after a lifetime in Fintech, working for US and Irish companies I am increasingly interested in working for a start up. Unfortunately a role I was interviewing for at an AI start up just got pulled so its back to the drawing board. Any advice you can offer in terms of how to search for these companies, most of the ones I find are US based and not always open to hiring remote from Europe.
Hi Colleen, unfortunately it's difficult for many people to work for U.S. companies being remote in Europe. If you are open to it, I would suggest bringing it up early in interviews that you are located in Europe and willing to work in U.S. timezones.
Dear Avelina26, My path was similar. I worked in around 11 startups, scaleups and unicorns in order to reach 6 figures.Congrats!I hope that you had fun and plenty support along the way.
Thank you for your support! I did have a lot of fun!
Thanks for sharing. This was incredibly inspiring to read!
Thank you for your kind comments.