Sydney Senior

Member

Happily Ambitious

A podcast about balancing achievement, expectation, and fulfillment in the world of SaaS, Sales, and Entrepreneurship. New episodes weekly.

Co-Host

RevGenius

RevGenius is a group of revenue generating Sales, Marketing, and RevOps professionals brought together to learn, share, support, and grow with each other. You can consider us your alt work family!

Deel

SMB AE

Sell Better 

Daily Sales Show Host

Falkon

Senior Business Development Representative

Pavilion

Chili Piper

Product GTM Manager

Associate GTM Manager

Trailblazer SDR

Chili Piper is the leading inbound conversion software, used by top B2B revenue teams like Intuit, Twilio, Spotify, and Gong.

We’re on a journey to build the best company to work for and to work with while trying to make the world a better place. Our team is distributed around more than 160 cities and 35 countries around the world. Join the movement!

Sales Development Representative

Brand30

Zgraph

- Conducted sales needs analysis with new and prospective customers
- Developed solutions based on specific client needs
- Maintained existing relationships with clients through regular communication and outreach

Account Executive

Kerigan Marketing Associates, Inc.

•	Certified in Google Ads and Google Analytics
•	Managed social media accounts and Google Ads marketing accounts
•	Created monthly performance reports for clients
•	Assisted with new website development and content migration

Social Media Marketing Intern

demystifying success & happiness | co-creator of Happily Ambitious | SMB AE @ Deel | building in public | mindset + productivity | Sell Better host

Feeling lost, stressed, burned out, or unable to get off the achievement treadmill?

Want to take design a life you actually love, but don't know where to start?

One of my biggest passions is demystifying success & happiness.

I've spent a lot of my life working incredibly hard (past the point of burnout) and still not feeling satisfied by my achievements, feeling like achieving one goal only meant that the goal post had to be moved further away from the next one.

While I'm far from having figured this out, I co-host a podcast (Happily Ambitious) and a companion newsletter (The Ambitious Breakthrough) to learn from some of the best in this area and share my journey as I go.

My goal is to build in public - through my role in SaaS sales, as a podcast host, as one of the founders of a growing community, and as someone who very frequently deals with all of the stressors described above.

Lead research and strategy across a 5+ product portfolio, partnering with executives, product, design, and engineering teams to derisk decisions, drive alignment, and shape roadmap priorities. Act as a trusted advisor to the Co-CEOs while scaling research operations and mentoring the design team.

Day-to-day, that means leading research across a 5+ product portfolio, from exploratory and user studies to competitive and win-loss analysis. I work directly with our Co-CEOs and senior leadership to shape product and pricing strategy, while enabling PMs, designers, and sales teams with the insights they need to move faster and with clarity.

Key Contributions & Impact
- Lead exploratory, user, product, competitive, and win/loss research to guide product and GTM strategy
- Delivered a new data-informed pricing model; currently defining a credit-based pricing system and platform-based packaging approach
- Implemented Rally UXR to democratize research and enable PMs/designers to run studies independently
- Conducted competitive deep dives to influence roadmap priorities and enable sales teams
- Drove alignment across 5+ product teams while mentoring designers and shaping customer narratives

Head of Research

It’s my job to infuse our design and development activities with user perspective and data as often as possible - to be the proxy to our users in all conversations and decisions. Day-to-day that means:
- Leading the UX and product research function 
- Overseeing all user testing and product research needs for our next generation of products
- Collaborating with Director of Design, Co-CEO, 5 Product Managers, and 4 Product Designers
- Working with PMs and Designers to define our next features and their specifications to best meet customer needs
- Managing vendor relationships for research tech stack
- Overseeing our pricing research and strategy
- Writing in-app copy for our next generation of products 

Tools I use regularly include: Chili Piper, Figma, UserVoice, Condens, SurveyMonkey, Miro, G-Suite

Lead Researcher

Chili Piper is the only inbound conversion platform, fueling high-growth B2B revenue teams. We solve interesting problems, live and breathe our core value of “help,” and have a ton of fun doing it while fully distributed worldwide — powered by espresso and hot sauce.

Senior User Experience Researcher

Helping companies light a fire under their SaaS 🌶

User Experience Researcher

Publicis Sapient

- Led the Chicago chapter of Women's Leadership Network
- Collaborate with clients to write testing protocol and script
- Execute usability and concept testing to inform experience strategy
- Perform ethnographic research to understand customer's clients' wants, needs, and pain points to inform an experience strategy
- Experience working with co-located, remote teams

Experience in the following industries: Transportation and Logistics, Supply Chain, Consumer Goods, Healthcare

- Collaborate with product owners and stakeholders to understand functional requirements
- Write and define functional requirements
- Communicate with development teams to ensure software meets specified requirements 
- Experience working with off-shore and co-located teams

Associate, Digital Product Management

- Global Semifinalist for the Publicis Groupe Client Impact Awards - February 2018
- Collaborate with product owners and stakeholders to understand functional requirements
- Write and define functional requirements
- Communicate with development teams to ensure software meets specified requirements 
- Experience working with off-shore and co-located teams

Junior Associate, Digital Product Management

Hub Group

As a Marketing Intern on the Sales Support team at Hub Group, I worked closely with the rest of the team to develop customer facing documents that encourage and grow sales. Request types included: Overview Presentations, Business Review Presentations, Proposals, Deal Wraps, completing RFP's and miscellaneous requests for sales representatives.

Marketing Intern

Whole Foods Market

Best Store in Company 2013, 2014
- Prepare 7-10 large-scale recipes items to specifications in a fast-paced, large, industrial kitchen at the company’s flagship store
- Work with team of 10-15 to ensure quality and timely preparation; delegate and lead by example

Prep Cook

Chicago Foodseum

- Collaborate with individuals and organizations in the surrounding area to secure donations / loans for our first exhibit, "The Hot Dog and Encased Meats of the World"
- Communicate with 3-5 brands and individuals daily to secure items / donations; write and execute loan agreements
- Coordinate all logistics in relation to the exhibit and donated artifacts; monitor exhibit design

Exhibit Manager

LifeTime Fitness

- Manage and train team of 3-5; prepare quick-service foods; extensive health-food knowledge
- Open/close store; prepare bank deposits; take inventory; minor buying& category management

Life Cafe Supervisor

I help teams make better decisions by asking thoughtful questions, surfacing the right insights, and translating what we learn into action.

At Chili Piper, I lead research and help inform strategy across our product and go-to-market teams. That means uncovering how our customers think, spotting patterns in messy feedback, pressure-testing ideas early, and guiding the team to prioritize what matters. I work closely with our Co-CEOs, product leaders, and design team to derisk decisions, shape roadmaps, and keep the customer voice front and center.

Some recent work I’m proud of:
- Helping define Chili Piper’s pricing strategy through customer + market research
- Synthesizing competitive intel from Gong calls to improve win/loss insights
- Driving product roadmap decisions across 5+ teams with evidence-based research
- Scaling research operations through Rally UXR and enabling PMs/designers to run their own studies

Outside of work, I’m usually reading on the couch, experimenting in the kitchen, planning the next national park hike, or brewing a new batch of beer. I also remain deeply (and often painfully) loyal to Chicago sports.

Always happy to swap stories or book recs. Let’s connect. 🍻

taplio

The Battle

Sydney Senior

Taylor Jennings

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