As I set up my own coaching business, I struggled with what technology to use and how to set it up. So I’ll pass along what I’ve learned to make your journey smoother. Where available I am using referral links which may pay me if you use my link to sign up.
Need personalized guidance? If you have questions about choosing or setting up your tech stack, getting started in the business of coaching, or pursuing ICF certification I offer paid mentoring to support your success.
Text Expander | Espanso
It seems like I type the same 10 things again and again: my website and socials, an invitation to connect, my favorite emojis. Espanso lets you create shortcuts – and it’s free! Basically, you update a text file with triggers that start with a colon : and then what you want to replace each of them with. I put some of mine below as examples. Now I type 2-8 characters and a whole string appears. Magic!
- trigger: “:dragon”
replace: “🐲” - trigger: “:chat”
replace: “I’m available for a 1:1 chat, grab a timeslot from my calendar: https://befriendingdragons.com/meet“ - trigger: “:li”
replace: “https://www.linkedin.com/in/cindygross“ - trigger: “:bde”
replace: “CindyGross@BefriendingDragons.com” - trigger: “:gptend”
replace: “Summarize what I asked, the general flow of the convo, and the outcomes as if we’re writing a short ‘what I did today’ note. Ask me why the conversation and/or the actions I completed mattered (the business impact). List any remaining action items. Don’t assume or add tasks I didn’t ask for. Help me celebrate what I accomplished in this convo.”
Client Portal | Coach Accountable
I tried several small business and coaching apps. Coach Accountable is hands down the best for both the client and coach experience. It has worksheets that you can associate with sessions, courses, or packages. You can assign clients to groups. Individual clients and groups have whiteboards, controllable access to courses, appointments, worksheets, action tracking, and metrics. The courses can be used to schedule worksheets, surveys, etc. The samples and knowledge base are excellent. It integrates with Stripe for invoicing and with multiple email and calendar clients. The owner holds regular office hours and answers questions on the forum. Best of all, most of the time when I think it can’t do something I need, I find that I’ve over-complicated it and there is simpler, cleaner option in the tool. Check out my resource kit with a starter course for new clients.
Coach Community | Coaching Corner
Coaching Corner is an incredibly supportive, friendly, and useful community of coaches. I’ve gotten tons of advice on how to price offers, how to connect with leads without feeling icky and overly salesy, and how and when to get certified in a 360 certification or ICF. There are regular online gatherings and lots of useful Slack conversations.
Podcast & Video Creator | Descript
I switched from Streamyard to Descript recently. Descript has several very useful AI features that help me create podcast episodes and videos with accurate captions. It’s super easy to create social media teaser clips, edit out filler words, and re-record a single sentence. It can auto-generate show notes and just generally make producing audio and video content easier and faster.
Image Design | Canva
Canva makes it easy to create social media images sized to fit various platforms. I also used it to create the icons on this site and all sorts of other images. I use the Pro edition because there are so many additional images included, it offers easy resize options, and I can save my fonts and colors as a brand so they are easy to apply as a style to my Pixistock templates.
Content Planner, Canva Templates, Stock Images | Pixistock
Pixistock offers a variety of Canva templates and stock images that are intentionally diverse and include a lot of culturally feminine elements. With an upgrade you get access to the “Content to Profit” content and a series of Masterclasses which are fabulous collections of worksheets and videos that help you define and deliver on your niche, package(s), content strategy, and visual brand.
Social Media and Broadcast | LinkedIn
As a leadership and career coach my content naturally fits with LinkedIn. I use it to connect with people I meet at community events, in my own events, and through referrals. I send a DM about where we met and what I do when I request a connection. I switched to creator mode so I can easily host events (either as a Live feed or with my Zoom link) and send newsletters.
Virtual Sessions & Events | Zoom
These days Zoom seems to be everywhere. Clients are likely to be familiar with it and familiarity can reduce stress for their first session. It’s also useful for lead generation events, webinars, trainings, etc.
Calendar | Calendly
Once a client purchases my coaching package all scheduling is done from within Coach Accountable. However, I still need to schedule meetings with people who want to have me speak at an event or on their podcast, interview me for an article, or who might be potential clients or partners. For that I use Calendly.
Lead and Client Management | Folk CRM
I found I rarely actually used my HubSpot starter account, it was a lot of work to figure out and maintain. Folk CRM doesn’t have all the features and options that HubSpot does – and that’s what makes it easy to use for basic operations. The main reason I went with Folk is that I can easily add folks from LinkedIn and add new LinkedIn DM conversations to Folk without having to pay for the LinkedIn Sales Navigator that the other CRMS rely on. The message templates are nice and easy to maintain.
CoWorking Body Doubling | Flow Club
Now that I work for myself, I can have a ton of trouble getting started on my task list and staying focused. What really helps me is planning out uninterrupted time and some low pressure commitments. So when I was introduced to Flow Club it was a game changer. I log on, choose a block of time from 30 minutes to 3 hours, enter a list of tasks, and work down the list with a group of silent people. This is called body doubling – the presence of other people helps us stay on track and finish what we start. The host may share music – you can mute it if it’s not what you need to hear. When I host a session I often play coffee shop background noise for the group and then a music playlist on my home speakers. I don’t know what it is about the mix of those two but it really helps my concentration. Click my referral link for a 2 week trial. If you like it you can become a host and get half off your subscription fee.
Sales Breakthrough Experience (AI Sales Accelerator) | The Laurens
This was one of the most game-changing experiences I’ve had for sales — and honestly, I didn’t expect to love it as much as I did. The Sales Breakthrough Experience helped me make sales feel aligned, grounded, and human. I got super clear on my ideal clients, created custom GPTs I now use in consults and client work, and finally built a sales process that feels like me. The tech support was smooth (even for folks who don’t speak “AI”), and I left with tools I actually use every day. If you want sales that feel like service — with just the right dose of nerdy support — check this out: Explore the Sales Breakthrough Experience.
Radically Generous Community | Coralus
I encourage others to join Coralus because it’s not just a funding community—it’s a radical, trust-based ecosystem that reimagines how we support women and nonbinary entrepreneurs. As someone who helps leaders Lead From Who They Are, Coralus feels like home: generous, collaborative, and future-focused. It aligns with my values of collective care, equity, and courageous transformation. This is what the next economy looks like—and I want to build it with people who are ready to do things differently.
Speaker Community | Innovation Women
Innovation Women is a community focused on supporting underrepresented voices to become successful speakers, presenters, workshop leaders, and facilitators. You can post your favorite abstracts so people can find you, and there is a long list of speaking opportunities with links to apply. The “green room” offers training on how to choose topics, write abstracts, and market yourself as a speaker. There are regular “Speaker Friends” meetups and opportunities to join events presented by members as well as staff.
Entrepreneur Community | Entreprenista
I joined a founder and entrepreneur membership community called The Entreprenista League. I’ve found incredibly smart, driven, like-minded women who are also kind and eager to help and support each other. In addition to the networking, partnership, and referral opportunities, I’ve found that The Entreprenista League provides tremendous lift for brand exposure. Every member gets a chance to be featured on Entreprenista.com and across their social channels.