Ep 202: Relationship-Led Pipeline with Jessica Lackey [Originally Live AMA]
Your pipeline doesn’t have to depend on algorithms, constant posting or a giant email list.
When I was figuring out who to invite to speak at the Solo Consultant Summit, Jessica Lackey was the first person I had in mind. If you’re trying to build a solo consulting practice, her name comes up again and again.
Jessica is the founder of Deeper Foundations and the author of Leaving the Casino. She helps experts become expert business owners.
This episode was originally a live AMA, and it’s packed with practical answers on building a relationship-led pipeline: how to structure it, how to scale it and how to keep up with it without living in your inbox.
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Relationships are the foundation of every business model
Jessica splits business models into two camps:
Delivery-based: consulting, coaching and agencies
Creator-based: monetizing an audience with courses, cohorts, memberships or paid newsletters
Relationship-led outreach is the obvious fit for delivery businesses. But Jessica argues it’s the foundation of creator businesses too. Even a paid Substack gets most of its subscribers through recommendations, collaborations and guest appearances. And you only get those through relationships.
The majority of my early work came from people I met through podcasting, so I’m nodding along.
The four stages of a relationship-led pipeline
Connection: New people get to know you.
Consideration: They see what problem you solve and how you solve it.
Sales: You invite them into a conversation about working together.
Champion: You stay in touch with clients, collaborators and connectors to create a flywheel.
Consideration doesn’t have to mean a newsletter. One of Jessica’s clients, a literacy educator, sells three or four long-term engagements a year. She hosts dinners, brings coffee to teachers on the first day of school, sends cards and gifts, follows up personally after conferences and reaches out every quarter. No newsletter. No social media.
Three ways to get introduced
Direct: Reach out to potential clients yourself, build a relationship and ask for introductions.
Brokered: Build referral partnerships with people who serve your clients.
Platformed: Ask for opportunities to share your message with someone else’s audience, like guest podcasts, summits and community teaching. This creates trust transfer.
The key is being as interested in helping the other person as you are in growing your network.
Yes, relationship marketing scales
Jessica tracked it. Over four years, she did about 50 guest appearances, 50 of her own guest teaching sessions and joined 17 communities.
Today she has a full roster of one-on-one clients, a membership of about 225 people and seven sold-out cohorts, built with a list of around 2,000 people.
She’s never had more than 1,500 Instagram followers. Her YouTube has about 500 subscribers.
It was slow. One appearance at a time. But now a meaningful percentage of her list buys from her every year.
CRMs: what to track (and what not to)
Jessica breaks CRMs into pipeline tools like Pipedrive, admin workflow tools like HoneyBook or Dubsado, and relationship CRMs like Folk or Attio.
She prefers relationship CRMs because you can create lists such as referral partners, prospects, connectors and past clients, then track what matters for each group.
But her bigger point: you don’t need a follow-up date for everyone. She only sets due dates for:
Sales opportunities
Visibility opportunities
Everyone else? If you talk to five different people every week, you’ll reach most of your network in a year.
For past clients, check in every six to 12 months about their goals, even if they’re not working with you. And if you sell into larger organizations, track multiple relationships within each account in case your champion leaves.
Cold outreach vs. borrowed audiences
Both can work. Cold outreach takes volume, research and follow-up, and you start with zero trust. Borrowed audiences bring built-in trust, though the rooms may be smaller.
Jessica’s advice: do both. Go warm when you can. Supplement with direct outreach when you need to. And if you go direct, be explicitly clear about the problem you solve. Nobody wants another pitch slap.
If you activate your network before you need people, you won’t need much cold outreach.
A campaign of helpfulness
Jessica borrows an idea from Mo Bunnell’s Give to Grow: when you meet someone new, don’t fire hose them with five resources.
Send one useful thing. Two weeks later, send another. Then check in again. Build a few helpful touchpoints over a couple of months instead of a one-and-done connection.
Get to know what’s important to them, who they want to meet and where they spend time. Then support them whether or not they’re paying you.
Another tip: you don’t need a newsletter to collect emails. One of Jessica’s clients wrote a thoughtful piece on rethinking workplace conflict, emailed it to her network and asked for their opinions. It got passed around and led to $50,000 in workshops.
Follow-up people actually answer
If someone says, “Let’s meet,” then ghosts you, make the ask smaller. Ask a yes-or-no question like, “Who should I loop in to get time on the calendar?”
If they still don’t respond, follow up quarterly with something valuable: an article, a resource or a question about what they were working on.
And don’t take it personally. Sometimes people just need reminding. (Guilty.)
Tier your network
Jessica doesn’t prune relationships as much as she focuses.
Tier one: 20–30 people who have sent business or are mutual advocates. They get holiday gifts and special cards.
Tier two: About 75 relevant people in her network.
Tier three: Everyone else.
Every year, she evaluates the health of her tier-one and tier-two relationships. If a referral partner stops marketing or a client contact changes jobs, she knows she needs to cultivate new relationships.
Snail mail and batching
Jessica is a big snail mail fan. She uses Postable to collect physical addresses and sends welcome cards, birthday cards and books to new clients.
The trick is batching. Instead of sending things whenever she thinks of someone, she runs campaigns: all referral partners at once, all past clients at once, birthday cards one week a month.
You can also hand repeatable “recipes” to an assistant, like pulling a list of contacts in a city you’re visiting and helping organize a dinner.
A meaningful personal touch once a year often goes further than you think because almost nobody else is doing it.
Winning executives in secret networks
Fortune 500 executives aren’t coming to online summits. To reach senior decision makers, Jessica recommends private and “secret” networks where real decisions get made:
Intimate dinners and curated roundtables
Associations and conferences
Alumni networks and paid communities
Social clubs, hobbies and private group chats
Ask your clients where they spend time. And if your network feels small, don’t only ask for introductions to clients. Ask for introductions to the people most likely to run into your clients.
Try this
Pick one idea from this episode and put it into practice this week. Maybe that’s choosing your tier-one relationships, sending five handwritten cards or following up with someone you met months ago with something useful.
Jessica Lackey
Jessica Lackey is the founder of Deeper Foundations, a consulting and training firm that helps expertise-based business owners grow and scale sustainable companies rooted in stronger business foundations. She brings a unique blend of corporate expertise and soulful business building, drawing on an MBA from Harvard Business School, a coaching certification from iPEC, and experience at McKinsey & Company and Nike, Inc. Jessica has supported over 200 entrepreneurs through her programs, blending systems thinking, operational rigor, and deep values alignment.
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