Long Story Short
Hoping deals close isn’t a revenue strategy. Building a sales system that helps you know where deals stand instead of guessing is. Don’t have time to read the full article? Steal Helia’s Pipeline Tracking Template from our Pipeline Tracking Toolkit to get started.
Jump to How!
Jess here!
Sales is one of those things that people think you either “have” or you don’t. Like it’s some innate gift — you’re a “salesperson,” or you’re not.
I don’t buy it.
What I’ve learned — from my time at Revolution Foods, from fundraising, from recruiting, from watching people who are really good at this — is that sales is both art AND science. It’s relationships AND data. It’s building genuine connections AND tracking your numbers. And most of us are only doing half of it (spoiler: the relationship half).
At Rev Foods, I remember those 100+ hour weeks when we were growing like crazy. I was deep in the work — calling districts, building relationships, trying to close deals. And I was burning out.
What shifted everything was when I realized I needed to pull in my “making things better” superpower AND surround myself with people who think differently than I do. We started meeting every one or two weeks for deep pipeline planning — really looking at the numbers, the conversion rates, where deals were getting stuck.
The results were transformational. We tightened up our pipeline and ran FOCUSED meetings. We analyzed which leads were moving to close and which were ghosting us. My team started having FUN. I started hearing ‘Jess, this is working!’ in meetings, and it was! We closed ~$18M on a goal of $14M — unheard of at Rev Foods at that time!
The salesperson I look up to (and I’m really good at sales!!)
Full disclosure: Emily Schaffer is one of my forever friends. AND, even if we weren’t forever friends, she’s still someone I’d look up to for how she brings equal parts warmth and rigor to everything she does, whether that’s building sales systems at YearUp, running apprenticeship programs, or figuring out how to make second chances actually work in the real world.
Her signature move? Emily doesn’t just DO sales — she builds the system, executes against it, and steps back monthly to review what’s actually working. She works ON the business AND IN the business. And that discipline — combined with actually tracking real numbers — is what separates hoping for the best from hitting your goals.
Here’s the other thing: everything Emily shares applies way beyond traditional sales. Fundraising? It’s a pipeline. Recruiting? Pipeline. Job searching? You guessed it. If you’re trying to move people through a process toward a decision, this is for you.
Sales isn’t about hoping deals come through — it’s about building a system and working it methodically.
The Key Takeaway
Sales isn’t about hoping deals come through — it’s about building a system and working it methodically.
The difference between scrambling and hitting your numbers comes down to two things:
- Tracking real conversion data at every stage of your pipeline
- Protecting time every single day to fill the top of that pipeline
No amount of relationship-building magic will save you if you can’t see where deals are stalling or if you’re not consistently feeding new prospects into the system.
Emily’s Pipeline Process
If you’re a “just give me the template, I’m ready to get started” kind of person (aka Helia’s COO Libby), Helia’s Pipeline Tracking Toolkit walks you through the folloiwng:
- Step 1 — Define your pipeline stages and assign likelihood percentages to each
- Step 2 — Protect time to fill your funnel (every single day!)
- Step 3 — Track your conversion rates and time-to-close at each stage
- Step 4 — Qualify people OUT of your pipeline — not just in
- Step 5 — Step back monthly to work ON the system, not just IN it
If you’re a “tell me why this works” kind of person (aka our Founder Jess), read on for the good stuff!
How Emily’s Pipeline Process Works
Step 1: Define your pipeline stages and assign likelihood percentages
“When you’re trying to hit an annual budget, the piece of sales that I always come back to is it’s really about numbers and a pipeline process.”
Before you can manage a pipeline, you need to break it into clear stages AND (most people skip this part) assign likelihood percentages to each one.
Emily’s stages and percentages (which you can see in her Pipeline Tracking Template):
- Lead (1%) — Just an idea, haven’t yet started the convo
- Initial Outreach (10%) — You’ve reached out or sent something but haven’t heard back
- Exploring (25%) — Live conversations are happening
- Proposal (50%) — You’ve submitted something official
- Verbal Commitment (80%) — They said they’re doing it!
- Contract Signed (100%) — It’s in writing!!
“You want to be conservative with those percentage metrics about your path to close,” Emily told me. Why? Because you’ll use this data to forecast revenue. “If your likelihood percentages are high, you’ll likely overestimate your revenue forecast and not hit your numbers.”
This works whether you’re selling services, cultivating donors, recruiting board members, or running a job search. The stages might look different, but the principle is the same: know where people are in your process and how likely they are to actually convert to the final stage.
Step 2: Protect time to fill your pipeline (every single day!)
“I set aside an hour every day just to fill the pipeline (also called a funnel) or move deals through stages. I can move that hour around my calendar, but I never double book it. Like, I never plan that I’ll do anything else other than fill the pipeline.”
This is the discipline that separates people who hit their numbers from people who are constantly scrambling. Here’s the secret sauce: Emily allocates her TIME in the shape of a funnel — roughly 50% prospecting, 30% moving leads forward, 20% closing. But her daily PRIORITIZATION flips it: close the urgent deals first, then move warm leads, then use the rest of the time to fill the top of the funnel.
“People get the prioritization, but they don’t save enough time to fill the top of the funnel. It takes more time than you realize. And if you don’t do it, you’ll run into challenges down the line.”
What Emily does in her funnel-filling hour:
- Direct personal outreach to people she’s MET (not cold emails to strangers)
- Attending events, exchanging cards, “really hobnobbing”
- Informational meetings where she’s asking for advice or learning about their business
- Following up with people who already know who she is
One thing Emily’s noticed: a lot of people think they’re filling their pipeline when they’re really just sending automated emails into the void. “All these tools like Apollo and ZoomInfo — people think they’re filling the funnel because they’re sending automated emails. Right now those emails are getting caught in spam filters. People aren’t interested. If it’s not yielding results, it’s not filling your funnel.”
Her approach is the best practice of salespeople from the beginning of time: Talk to someone face to face. “My first point of contact is always a live connection — Zoom or in person. I really do reach out to a lot of people I know.”
Step 3: Track your conversion rates and time-to-close at each stage
“You want to be looking for how many people move through each stage of the funnel. What’s your conversion rate? And then that helps you anticipate where you think you’re going to land at the end of the year.”
Here’s where the math gets powerful. If Emily has 20 people in “Exploring” with a 25% conversion rate, she knows roughly 5 will move forward. If she needs 10 contracts by year-end, she knows she needs to get more people into the “Exploring” stage (at least 20 more!) — or she needs to figure out why conversion is lower than expected.
“You can figure out which parts of your process are not performing based on the conversion rates and the data at each phase.”
Emily learned this lesson the hard way at YearUp. One cycle, they were off by a significant number of internships. When they dug into the data, they discovered their renewal rate had dropped from 96% to 73%. Still high — but their model hadn’t anticipated it.
“We had to turn all of our account managers into business development people for a couple months” to fill the gap. “Our time to close was about six months. So if you weren’t six months ahead of your needs, your ability to make changes in the moment was pretty limited.”
The lesson here: Plan ahead or scramble later!
Moving a lead to “Closed Lost” isn’t failure. It’s clarity.
Step 4: Qualify people OUT of your pipeline — not just in
Once someone’s in the funnel, salespeople have a tendency to want to keep them in the funnel until they say no. But if you don’t hear the no and it’s just a delay, your time is being wasted. You need to have some time-bound rules about when to move someone OUT of the pipeline yourself.”
This can feel counterintuitive to anyone who likes the “security” of a full pipeline, but it’s one of Emily’s most important moves. Set rules for yourself: “We’re going to do outreach for a follow-up three times over a certain period of time. And if they aren’t responsive to that, we’re going to consider them Closed Lost.”
Why does this matter?
“You’ve got to gain insights from your active pipeline. You need to know what types of leads are never going to close so that you can focus your time on the leads that will. And if you have a bunch of stale leads that aren’t actually going to close, they distract you from what the data is actually telling you.”
Here’s the practice: when someone goes dark, you move them to “Closed Lost” in your pipeline. But — and this is key — you create a recurring reminder to revisit your Closed Lost list regularly. Maybe it’s quarterly, maybe it’s at the start of each fiscal year. Emily puts it this way: “You can always put those people back in your pipeline. You can always re-engage them at the start of the next year and say, ‘Hey, we had a conversation a while ago. Is this something you’d like to explore this year?'”
Closed Lost isn’t a failure — it’s clarity. And it keeps your active pipeline clean so you can actually see what’s working.
Step 5: Step back monthly to work ON the system, not just IN it
“It’s very easy to spend your time on sales calls or meeting new prospects, but it’s really valuable to take a step back — maybe on a monthly basis or quarterly basis — to look at things from a bird’s-eye view. I review the pipeline, assess the time spent in the pipeline, the time spent to close, how my pipeline is performing, and whether my stages are defined accurately.”
Emily treats this like a board meeting with herself — no distractions, just honest assessment.
Emily’s monthly pipeline review checklist:
- Run a report showing how many opportunities you have at each stage
- Compare with the prior quarter’s report
- Calculate your conversion rates (percentage moving from stage to stage)
- Calculate time to convert (average time folks spend moving through each stage)
- Look at both year-over-year AND quarter-over-quarter trends
- Reconcile everything back to the anticipated revenue
“I don’t believe it’s effective to do those practices mid-day between a bunch of sales calls. You’re not in the right mindset. I just don’t think it works.” You need distance to see patterns and make strategic adjustments.
This is the difference between running around following someone else’s process OR building a system YOU designed because YOU know your market and your customers. When you work ON the system AND IN the system, you’re actually tee’d up for success.
When to Do This Yourself vs. Bring Someone In
A lot of this you can absolutely do on your own. Set up your pipeline stages, block time for funnel-filling, and start tracking your numbers. Emily’s template gives you the structure — you just need to fill it in and commit to reviewing it.
But you might want outside help if:
- You’ve been tracking for a few months and can’t figure out why conversion is stalling at a particular stage
- You’re building a sales function from scratch and want to get it right the first time
- You’re transitioning from founder-led sales to a team approach and need help designing the system
- You keep saying you’ll block time for pipeline work, but it never actually happens (sometimes you need accountability!)
If You Want Help
Emily Schaffer helps leaders build sales systems that actually work — combining the relationship piece with real data discipline.
She’s a good fit if:
- You’re responsible for revenue, but don’t have a clear pipeline process
- You want to get strategic about sales without losing the human element
- You’re stuck in the “it’s faster if I just do it myself” trap
Connect with Emily!
Try it Yourself
Helia’s Pipeline Tracking Toolkit:
- Our Pipeline Tracking Template — the actual spreadsheet we use, with stages, likelihood percentages, and revenue projections built in
Recommended reads:
- Miller Heiman’s SPIN Selling for sales methodology fundamentals
- Active listening training (Emily says this was the best sales training she’s ever done — better than actual sales training because it taught her to hear what prospects actually value)
Questions to Sit With
- What percentage of your time are you actually spending on filling the top of your pipeline versus moving existing prospects? (And be honest — is that sustainable?)
- When’s the last time you stepped back to analyze your pipeline data instead of just hoping this month will be different?
- Are you asking prospects what problem they’re trying to solve, or are you pitching what you think they need?
- Do you have an hour blocked on your calendar right now — like literally this week — for filling your funnel? (If you just said “I’ll find time,” that’s a no. Go block it before you close this tab.)
Not sure Emily‘s the right fit? Talk to Helia directly!
This article comes from a coffee chat with Emily Schaffer in October 2025. These conversations form the heart of the Helia Library — because we’ve learned the most from doing and from talking with other doers willing to share their wisdom. We don’t need to start from blank pages or do everything alone.
As always, take what’s helpful, leave what’s not, and make it your own.
About Emily
Emily Schaffer has spent her career figuring out how to make opportunity actually accessible — from building sales systems at YearUp that placed hundreds of young adults into Fortune 500 internships, to running apprenticeship programs that give people real second chances. She’s the person who will ask you the hard questions about your numbers AND remember to ask how you’re doing.
