“Just having the courage to allow some of your real story to come through publicly is your differentiator. It builds trust, opens doors to sales conversations, and draws future customers to you.”
–Jess Jensen

Jess Jensen, co-founder of Co-pilot Communications, is back for the second part of this powerful conversation. In part one, she revealed why your personal story is the ultimate marketing tool. Now, she’s sharing how to put it into practice with a clear, step-by-step framework for building a digital presence that feels authentic, consistent, and achievable.

From breaking through inconsistency, to leveraging AI for content ideas, to showing just the right kind of imperfection—Jess shares practical strategies small business owners can use to show up online and grow their influence.

In this interview, you'll learn…

• How to overcome the biggest barrier to showing up online: inconsistency

• Why the right kind of imperfection can make you more trustworthy than polished content

• How AI can accelerate your content creation while still keeping your voice authentic

To learn more about Jess, click here.

Connect with her on LinkedIn.

Bonus for listeners: Jess is offering a free 25-minute LinkedIn audit during October. Visit copilotcommunications.com and mention you’re a listener of The Successful Bookkeeper to claim your session before spots run out.

Time Stamps

00:00 – Why courage & vulnerability build trust
01:25 – Simple ways to dip your toe into posting
02:20 – Why responding matters more than likes
04:04 – The real barrier: inconsistency
06:17 – How AI can help with idea generation
09:06 – Treating AI like a junior employee you train
12:08 – The psychology of showing up online
14:38 – Imperfection as a powerful differentiator
18:16 – Why collaborators & “yes/no” people matter
18:58 – Where to find Jess online & claim your free LinkedIn audit

This episode is brought to you by our friends at Dext!

Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place.

Join thousands of bookkeepers and accountants who’ve already made the switch.

If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you!

Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!

"People are interested in other people. So you can talk about your practice or where you see perhaps the industry going down the road, but from a point of view that is informed and experienced and maybe has a little bit of vulnerability woven in.”
-Jess Jensen

Jess Jensen, co-founder of Co-pilot Communications, has helped leaders at Microsoft, Qualcomm, Adidas, and now small business owners across North America build their digital presence. In part one of this two-part series, she shares why personal storytelling is key to standing out in today’s crowded market.

In this interview, you'll learn…

• Why personal voices connect more than brand voices
• How storytelling humanizes small businesses
• Ways to overcome fear & self-doubt
  

To learn more about Jess, click here.

Connect with her on LinkedIn.

Time Stamp

00:00 – Why people connect with personal stories
01:23 – Journey from global brands to co-founding Co-pilot Communications
03:16 – Helping executives build digital platforms
04:31 – Humanizing brands through leadership voices
06:47 – Applying storytelling to small businesses
09:52 – Overcoming fear & finding your voice
13:45 – Differentiation: “Differences sell, similarities don’t”
16:08 – Step 1: Define your “audience of one”
20:28 – Step 2: Clarify what you want to stand for
24:38 – Step 3: Practice creating content & iterate
25:41 – Step 4: Build relationships in the comments
26:46 – Preview of part two: Jess’s full four-step playbook

This episode is brought to you by our friends at Dext!

Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place.

Join thousands of bookkeepers and accountants who’ve already made the switch.

If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you!

Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!

“A woman came up to me and said, ‘You know, you really get me.’ And I thought that's really the mantra I want to kind of go with. I want people to understand that I get what they're saying. I can't be them, but I can translate the pain and the successes that they're having.”
-Jennifer Kahnweiler

Introverted leaders bring unique strengths to the workplace, but they’re often overlooked. In this episode, Jennifer Kahnweiler, an expert on introverted leadership, shares how introverts can thrive, influence, and lead with confidence.

In this interview, you’ll learn:

• How the Four Ps help introverts succeed in leadership
• Practical ways introverts can influence without being loud
• How listening can become a powerful sales advantage

To learn more about Jennifer, click here.

Connect with her on LinkedIn.

Time Stamp

00:00 - Introduction to Introverted Leadership
01:57 - The Journey to Understanding Introversion
05:31 - The Evolution of Introverted Leadership
11:21 - Creating Introvert-Friendly Workplaces
14:48 - The Impact of COVID on Introverts
19:42 - Navigating the Changing Workplace
21:01 - Empowering Introverts in the Workplace
22:54 - Embracing Introversion in Leadership
24:27 - The Evolution of the Introverted Leader
26:20 - The Four P's of Introverted Leadership
32:24 - Listening as a Key Skill for Introverts
38:08 - Recognizing & Valuing Personal Accomplishments

This episode is brought to you by our great friends at Sage!

Drowning in paperwork?

AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients.

Learn more about AutoEntry or get started for free at Sage.com.

“ I think it's important that you go for it. You imagine what that looks like. I didn't go into this with the intention of having a big company. It happened one employee at a time. How do you get the 30 employees? Well, start with one.”
-Jenny Groberg

In this episode, we wrap up a two-part conversation with Jenny Groberg, founder of BookSmarts Accounting and Bookkeeping, where she shares how she turned a small team into a high-performing force, overcame personal challenges, and scaled her business to seven figures.

In this episode, you’ll learn…

• Raising expectations & setting clear boundaries
• How to delegate effectively to focus on growth & leadership
• Adopting subscription pricing to streamline billing & boost cash flow

To learn more about Jenny, click here.

Connect with her on LinkedIn.

Time Stamp

00:01 – Transition from hobby employees to a committed team
03:55 – Personal recovery journey & building a supportive culture
05:30 – Giving back through scholarships, donations & teaching
12:36 – Shift to subscription pricing & improved cash flow
21:00 – Letting go of toxic clients to safeguard staff
26:36 – Encouragement to set big goals, delegate & believe in yourself

This episode is brought to you by our great friends at Sage!

Drowning in paperwork?

AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients.

Learn more about AutoEntry or get started for free at Sage.com.

“ When I'd go on appointments I would say, ‘You know, I do work with so and so’, and then that would kind of just help them feel reassured that I knew what I was doing, but I never pretended to know everything. I would be very upfront. If there's something I don't know, let me do some research and I'll get back to you.”
-Jenny Groberg

Jenny Groberg, founder of BookSmarts Accounting and Bookkeeping, shares her powerful story of building a seven-figure firm from scratch. Listen to this episode to learn how small actions can lead to big wins in your bookkeeping business.

In this episode, you’ll learn…

• How a $500 QuickBooks certification launched her business
• Why asking for client reviews changed everything
• Ways to scale while balancing family life

To learn more about Jenny, click here.

Connect with her on LinkedIn.

Time Stamps

00:01 – Jenny’s start in bookkeeping with no money & two kids
02:43 – The $500 QuickBooks investment that paid off
03:32 – Asking for reviews & building credibility
08:33 – Turning small clients into long-term relationships
17:03 – Hiring the first employee & scaling the team
19:52 – Overcoming setbacks & a traumatic brain injury
31:30 – Keys to growing a seven-figure firm

This episode is brought to you by our great friends at Sage!

Drowning in paperwork?

AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients.

Learn more about AutoEntry or get started for free at Sage.com.

“ One of the most famous quotes ever from Tony Robbins, this one I take with me every single day. ‘Fall out of love with yourself and fall in love with your customer and watch the magic happen’. And you gotta fall in love with your customer. When you fall out of love with what you offer or your package, and you fall in love with your customer, you have a beautiful relationship that happens.”
-Lynn Gagne-Webb

In this episode, we wrap up our two-part conversation with Lynn Gagne-Webb, founder of Custom Bookkeeping. Lynn dives into the challenges of pricing, managing client expectations, and building a bookkeeping business that truly fits your goals.

In this episode, you’ll also learn...

• Why understanding communication styles can transform client relationships
• The pros & cons of hourly billing versus value-based pricing
• How to handle scope creep without burning out your team

To learn more about Lynn, click here.

Connect with her on LinkedIn.

Time Stamp

01:00 – Intro to part two with Lynn Gagne-Webb
01:44 – Trust & communication with clients
03:26 – Color coding for better communication
05:14 – Airplane analogy for pricing & expectations
08:33 – Handling clients wanting more for less
17:13 – Switching from packages to hourly rates
19:54 – Managing rising costs with the airplane model
24:14 – Flat rate questions & subscription fatigue
28:56 – Adapting to industry changes
31:43 – Focus on loving your customer
32:21 – Courses & Learn Bookkeeping Canada

“ You're on your own as a business owner. You're trying to figure out, there's no course that anybody gives you to tell you how to be a business owner.”
-Lynn Gagne-Webb

In the first of a two-part series, Lynn Gagne-Webb, founder of Custom Bookkeeping, shares her journey from the corporate world to running and selling a successful bookkeeping firm. As well, Lynn dives into her unique approach to building a team, and reveals how creating a culture of trust and flexibility helped her attract and keep loyal staff for years.

In this episode, you’ll also learn...

• The struggles of being a business owner
• The importance of taking CEO time to review your own business health
• How to focus on leading your business

To learn more about Lynn, click here.

Connect with her on LinkedIn.

Time Stamp

01:23 – Lynn shares her journey from corporate to entrepreneurship
03:37 – Lynn’s vision for supporting small business owners
04:18 – The challenges of being on your own as a business owner
05:22 – Why small businesses struggle & how lack of knowledge hurts them most
06:41 – Getting caught up in growth & forgetting to review your own numbers
07:51 – The value of CEO days & looking at your business health
08:49 – Why even bookkeepers shouldn’t do their own books
10:17 – The difference between detail-oriented & problem-solving bookkeepers
12:22 – Knowing your strengths & weaknesses as an owner
15:38 – Lynn’s hiring experiences & lessons learned in building a team
18:14 – How flexibility & trust created a loyal workforce
22:12 – The impact of culture on retention & business success

“But we just don’t have the time if we're on the gerbil wheel of doing the same thing over and over again every month is just a new month. Where do I find time to ask three or even one new question when I'm busy doing the stuff that I have to do, and we've got to focus our attention on fewer clients, but deeper work for those clients. And that's when we create the capacity to do the kind of work that matters to those clients.”
-Geni Whitehouse

In the finale of our two-part conversation with Geni Whitehouse, she shares practical tools and mindset shifts to help you step confidently into advisory and build stronger client relationships.

In this interview, you’ll learn..

• Why mindset, not skill, holds most bookkeepers back from advisory
• How DISC behavior styles improve client communication
• Why listening is your secret superpower

To learn more about Geni, click here.

Connect with her on LinkedIn.

Time Stamp

01:06 - Doing deeper work for fewer clients
03:00 - Using humor & storytelling
05:15 - DISC behavioral styles
08:18 - Listening as a key advisory skill
10:01 - Importance of aligning meeting style with client behavior
11:58 - Why Flexibility leads to more relevant outcomes for clients
14:57 - “Mindset, Toolset, Skillset” framework
15:40 - Mindset shift
17:56 - Focusing on fewer, higher-value clients
23:01 - Biggest mistake: not starting
25:50 - Prioritizing client impact over fear of failure
29:03 - Geni’s websites and how to join her training programs