The Jill James

Advisory support services for self-funded founders who want on-demand expert support and a quarterly review of their business.

Advisory Guidance

A free, weekly newsletter written for self-funded founder / CEOs who want to achieve their personal goals in a for-profit, high-impact business. Sign up at thejilljames.com/newsletter.

The Jill James Newsletter

Our flagship consulting engagement is the Business Design Reboot. We work with up to 10 new clients annually for an initial 6-month engagement, working 1:1 with you to define your personal playbook and roadmap for building your company.  

First, we define what you want. Then we design your business to meet your goals - high growth, great benefits, paying yourself and others, working a four-day week. You choose the pieces, we solve the puzzle.

That's part one. Now that we've got a roadmap, you’ll need to change how you work, and fast. We’ll support you in implementing that strategic operating plan. You focus on sales, customers, and products. We make sure you've got advice, finance, pricing, operations, partners, and compliance support. We'll put systems and procedures in place so you spend less time running your business and more time building it. 

In this process, we answer questions like: 

- How can I bring my purpose into my company? 
- How can I do more of the things I love?
- How can I be more profitable?
- Am I spending the right amount on my operations? 
- Should I hire people?
- How much can I pay myself?
- How can I be smarter about taxes?

You get: 

- A written 12-month strategic plan and sales forecast, with numbers and financial projections
- A set of offers or products priced for profitability goals  
- A staffing and operations plan
- Six months of executive support and accountability 

Is the Reboot for you? Let's find out - grab a free 20-minute strategy session with me at thejilljames.com.

Business Design Reboot

Three Day Rule

Functioned as COO, CFO, and CMO for personalized matchmaking services and technology company from product/market fit to Series A completion. Grew run rate to $2.5 million with path to profitability. Expanded from two to six metro areas and 2 to 30 full-time employees.

Real Media Group - a division of 24/7 Media Inc.

Fulfilled my commitment to the Panache earnout following acquisition by WPP. Reconcepted the video offering for agencies and brands and led growth of North America video ad network.

Panache

Pivoted the firm from platform professional services to a digital video workflow and ad product solution that drove sales development to reach EBITDA break-even for exit. Acquired by WPP PLC for a multimillion dollar, undisclosed amount.

VP, Marketing

Razorfish

Learned everything digital marketing, e-commerce, creative, SaaS, analytics, media, consumers, kids, and moms from the best in the business. My favorite part was putting Barbie on Facebook. Clients included Mattel, Disney-ABC  Television Digital, SOAPnet/ABC Daytime, Walt Disney Parks & Resorts (WDPRO), LA Metro, and Munchkin.

Account Director

Offermatica

We helped progressive brands test and optimize their e-commerce sales and marketing. Designed and executed e-commerce marketing optimization programs for Fortune 500 marketing departments including Sears, Intuit, T-Mobile, Blinds.com, Fandango, and Kelly Blue Book. The professional services arm of Offermatica, an Accel-backed venture acquired by Omniture ($65M), now Adobe Site Catalyst Test and Target.

Client Manager, Otto Digital

Zimbra

Back when there were only a few SaaS products, launched first two open source web-based collaboration suite products. We helped a lot of large companies give everybody an email inbox. The company was backed by Accel and Redpoint and was acquired by Yahoo! ($350M), now VMWare Zimbra.

Product Marketing Manager (Internship)

AXA Financial, Inc.

Where I got my first taste of supporting a CEO. I spent every day with the CEO and executive team to support our insurance, direct sales, and mutual fund operations in the US. Wrote speeches, ran offsites, evaluated opportunities, worked on mergers, looked for opportunities to improve the company, generally wrangled. 

Before that, I spent two years advising individuals and small businesses on their personal and business financial planning and wealth management.

Project Analyst to the Chairman & CEO

Afternic.com

In the dot com boom, figured out how to automate our services for scale and build internet software for trading stuff. Ran post-auction settlement for global domain name marketplace acquired by Register.com ($60M); defined business requirements, added relationships for escrow and credit card processing.

Commerce Strategy Manager

J.P. Morgan

Managed $150 million leveraged lease portfolio while restructuring to release $30 million in cash to the business unit.

Analyst

I help self-funded business owners build and run profitable, purpose-driven companies through strategic operations support.

When you started your company, everything was fresh and exciting, especially the flexibility. But running the company has become a dull and overwhelming chore. You're having the Sunday Scaries (and the Tuesday Terrors and the Friday Fears). You're not enjoying the work. The day-to-day of balancing growth with HR, finance, and management is tedious. You've lost the joy. And you're wondering, do I really want to keep running this company? 

At the same time, you want to make a positive impact on the world with your work. And you don't want to go back to a 9-to-5 job. You are determined to figure this out.

It's hard to build and lead a company while you learn to manage it, and not lose your focus on impact. I use my background in strategy, operations, finance, and growth management to be a general management partner to self-funded founder/CEOs like you, who are navigating building for-profit companies that balance impact on the world and financial stability for themselves. 

I work with founder / owners who:

- Want to grow their self-funded company to the high 6 or 7 figures, but currently feel stuck
- Know they need a playbook and roadmap that achieves or exceeds their work and personal goals
- Have a non-negotiable mission, purpose, or impact goal 
- Don’t plan to take institutional equity investment 

I help you:

- Design and build a strategic roadmap specifically for YOUR company
- Run your company as a general management partner 

What other founders have said:

💬“I worked with Jill on our operations and growth strategy. Our growth has landed us on the Inc 5000 for five years. We continue to rely on Jill as a trusted advisor as our business evolves.”
 -Amber Allen, Founder & Chief Strategist, Double A Labs

💬 “Jill’s direction and expertise have been instrumental in our company’s year-over-year growth, guiding us from a small startup through our recent recognition as one of the fastest-growing private companies in America. We would highly recommend her services for any size company looking to improve operational stability, leadership, and growth.”
-Brian Loschiavo, Co-Founder, Riverside Entertainment 

Have a vision but you’re not sure of the steps to get there? Drowning in admin yuck? Get my support, education, and access to live Ask Me Anything Q&As by joining my list at thejilljames.com. (There's also a link to book a free 20-minute advice call.)

I usually quiet quit vendors who aren't performing, but Take Command really deserves to a shoutout for cancelling multiple client QSEHRAs six weeks early, deleting all the related reimbursement files, forcing us to use an AI chatbot with wrong information, sending me in circles with an offshore support team that can only tell me that no accounts exist, and providing a benefits manager "hotline" that requires me to clear my schedule for hours of wait time. 

They took at $25 million equity investment in 2023 from Edison Partners and their "playbook" has been to enshittify what was a quality small business service.

Companies with fewer than 25 employees don't have dedicated HR managers. Small businesses are already being hit hard by the economic and political environment. We're just trying to do the right thing and give employees access to health insurance. 

Be an ally, not an impediment. 

PS, while writing this, I reached the 1 hour hold mark. A recorded message came on to say "You call has been logged, thank you for contacting us" and disconnected. That's evil.

UPDATE: thank you to TC team for taking action to repair this situation. I have spoken to the head of customer support and we are on our way to putting things right.

Jill James

Hi there, fellow self-funded founder! We're 98% of American business owners. Yet most of the advice out there assumes we've got equity investors and are just burn burn burning through that sweet moolah.  

So what's a self-funded founder to do? There's a lot to learn in your journey from founder to CEO. It might feel like your idea is getting lost while you're figuring out how to run a company. Or the flexibility you loved at the beginning is impossible to get back. 

Let's re-ignite your excitement. Let's make it easier to find and focus on the things that actually make a difference, that drive sustainable growth. 

For founders who have ambitious visions for their self-funded companies, The Jill James is a strategic operating partner that sets the foundation and scaffolding for sustained growth. Unlike coaches and gurus who focus only on mindset or feed you one-size-fits-all tactics, The Jill James will design YOUR business, aligned to your values and goals. 

My team brings the elite operational support, expertise, and sounding board to you. This allows you to honor your vision, let your business grown with intention and purpose, and know you do not need to make every decision alone. 

I help you move from founder to CEO. 

My background in entrepreneurship and strategy. I have a proven record of helping start-ups gain the operational knowledge they need to thrive, increase profits, use non-equity funding sources, and accelerate growth. Blending my 12 years in tech start-ups, experience as a financial planner and banker, and love of early-stage companies, we will also focus on tax saving and personal wealth tools as part of your success plan.  

I work with people who are ready to confidently claim their role as CEO. Learn more at thejilljames.com.

Design, grow, and run profitable, self-funded, impact-driven companies. Business design, strategy, operations, and finance.

Last week, I listened to a podcast interview with UCLA women's basketball coach Cori Close. I scrawled this note on a post-it:

How can I be transformational in a transactional world?

Yes, we all need to be decisive. We need to sell things, save and invest money, hire and downsize at times. 

But how do we make space to develop as people and have a lasting impact? Is it just the X's and O's of work for you, or are you here to lead?

That's something I'll be thinking about this week. (It was not on the inside of my eyelids, contrary to what the accompanying art suggests.) 

What do you think?

You have all the jobs.

When you're self-funded, you're not just the CEO. You're HR. Finance. Sales. Compliance. Facilities. 

And this time of year? It’s all of that, plus trying to close the books, keep up your sales pipeline, and show up for your people, at work and at home.

Your time is precious. That's why I use this time of year in my newsletter to focus on getting you to the end of the year without missing opportunities and with a shred of sanity. 

As one subscriber put it:
"It's one of the few newsletters I get that I always read, and I really like that the focus is on business ops and entrepreneurship."

Every week, I share things I've learned as a consultant and small business owner, like strategy, tax savings, hiring, compensation, and the hard decisions about how to build something that works for you.

No fear tactics. No mastermind sales pitch. Just profit-powered growth that's authentic to you. 

Come see what it’s about.
📩 Subscribe here: https://lnkd.in/gvg9EWCD
📚 Browse recent issues and excerpts.
📢 And yes, audio’s included if you’d rather listen than scroll.

They say the devil is in the details. In yesterday's newsletter, I talked about a little January devil that can tank your most ambitious hopes and dreams for January 2026. You’re building your pipeline. You’re taking sales calls. You’re fully in the New Year, New You mindset. And then you get my January 14 email, and it all comes to a screeching halt. 

That’s going to be your reminder that your 1099s and W-2s are due by February 2. 

You’ll stop building your business while you chase consultants and freelancers for W-9s. You’ll be scraping year-old bank transactions and running data merges to produce teeny-tiny forms. 

But not this January, because you’re going to get organized right now.

https://lnkd.in/gVeWdvNT

Right now is the moment when small business owners like you can make a single decision that shapes your financial future: whether to open and fund a 401(k) plan before year-end. For many of you, this may be your best chance to save tens of thousands of dollars for yourself instead of sending it to the IRS. 

Read the latest newsletter to decide if a 401(k) is right for you—and how to choose a provider before year-end. 

📩 https://lnkd.in/gxfU-3Ea

It's crunch time for health insurance open enrollment. If you're buying through an ICHRA, here's a quick tip on how to find value in off-market Silver plans, shared by Venteur in our recent live event. 

While your state marketplace choices may have shrunk, insurers are offering off-market Silver plans on ICHRAs. These plans can be 10–12% cheaper than traditional group plans, and come with more support.

Check out this clip for more tips.

It's crunch time for health insurance open enrollment. We've decided to open up access to the replay from the self-employed health insurance event I held for my newsletter subscribers. 

We cover ACA-compliant exchange and off-exchange options and individual eligibility for 2026 subsidies. I also have a updated guide and glossary of terms on my blog, which was posted earlier this week.

https://lnkd.in/gtzmJevM

The open enrollment roller coaster continues. Will subsidies be re-extended? What do you qualify for now? And will we get better information before the December 15 enrollment deadline?

I wrote my 2026 Health Insurance Guide back in October, but with so many updates to healthcare.gov on November 1, I've revised it to support you in this final stretch. 

The big thing we’re seeing? Everyone pays more.

Even with subsidies, everyone pays a monthly premium. But that’s just the start. Between deductibles, co-pays, co-insurance, and out-of-pocket maximums, there's a lot to consider in your total cost of use.

ACA-compliant plans still include preventative care, well child visits, pregnancy, vaccines, and some chronic care support before your deductible.

All Bronze plans now qualify for HSAs, as do Silver HDHP plans.

Some states have added noncompliant Catastrophic plans for those who have lost their subsidies and can't afford a Bronze premium.

Check out my updated guide with everything we’ve seen so far:
🔗 https://lnkd.in/gPx3zt3z

Got year-end questions? Send them my way.

I am saving space in an upcoming newsletter to for a Mailbag roundup from readers. If you have questions about running or growing your business, this is your chance -- let's hear them!

Some possibilities:
- Year-end planning
- Health insurance choices for 2026 and open enrollment
- Pricing, margins, and cash flow
- W-2 pay, owner distributions, and retirement savings
- Contractors and hiring
- Systems, operations, technology, marketing, legal, HR
- Team policies

Email your questions to hello@thejilljames.com. Voice memos are welcome, too!

I will answer as many as I can in our Mailbag newsletter edition.

December, we hardly knew ya. Two major holidays and the end of the tax year do not play well together. When you get crunched, what might you skip until January?  

• Year-end bonuses
• 401k profit sharing
• SEP IRA setup or contributions
• Year-end distributions or owner draws
• Updating your employee handbook

Talk to your tax advisor about what's a 2025 must and what can collect a little dust.

If you’d like some support with your end-of-year strategy, schedule a free 20-minute Strategy Session with me.

🔗

taplio

Jill James's Linkedin Analytics

Jill James

Performance ScoreJill James's LinkedIn Performance

Jill James's Best Posts (last 30 days)

Ready to grow your LinkedIn presence?

taplio

.css-6ytdur{background-image:linear-gradient(284deg, rgba(39, 43, 72, 1) 0%, rgba(33, 47, 183, 1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Jill James's Linkedin Analytics

Jill James

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jill James's LinkedIn Performance

Jill James's Best Posts .css-1emoo84{font-size:var(--chakra-fontSizes-md);font-weight:400;color:var(--chakra-colors-gray-600);}(last 30 days)

Ready to grow your LinkedIn presence?

Jill James's Linkedin Analytics

Performance ScoreJill James's LinkedIn Performance

Jill James's Best Posts (last 30 days)