8 Ways To Improve Your Outbound Sales

1. Key Themes

Manual Effort Before Automation Is Non-Negotiable

Christina Gilbert argues founders sabotage themselves by automating before they understand what works. Blasting messages without learning creates a dead end where failure teaches nothing.

"If you get zero replies from a campaign that you didn't give any thought to in the first place, then at the end, when you have zero replies, you've learned nothing." 00:00:38 "So my recommendation is to do at least 100 outreaches by hand before you automate anything." 00:00:38

Targeting Matters More Than Message Quality

A perfectly written email to the wrong person will never convert. Gilbert stresses that founders waste enormous time polishing copy while ignoring who receives it.

"Outbound prospecting is kind of like looking for a needle in a haystack. You need a person that has the exact pain point that you solve, or a perfectly crafted message won't even land." 00:01:34 "Those wrong job titles were never going to buy, no matter how good your email was." 00:02:02

Intent Signals Are Product-Specific and Discoverable

Every product has unique signals that indicate a prospect company is ready to buy — headcount thresholds, job postings, growth stage — and finding them is a core founder task.

"Companies below 100 employees probably aren't introducing levels for their employees, so they won't need your software... Every product has signals like this. Your job is to discover yours." 00:03:28

The Email's Only Job Is to Prove You Understand the Buyer's Pain — Not Explain the Product

Executives don't care about features; they care about their own risk and incentives. The product pitch should be a single sentence at most.

"The truth is that executives don't care about your product features. They don't care that you have blazing fast uploads. They don't care that your database is built in rust. They're worried about how they're going to hit their quarterly target." 00:04:48

LinkedIn Profile Optimization Is an Underrated Conversion Lever

Profile picture, banner, about section, and mutual connections directly affect reply and acceptance rates, functioning like a "subject line" for LinkedIn outreach.

"If email has subject lines, LinkedIn has your profile." 00:07:13 "The number of shared contacts is the single biggest predictor of whether or not somebody is going to accept your connection request in the first place." 00:08:11

A Structured Debugging Order Diagnoses Low Reply Rates

Gilbert has a specific sequence for diagnosing broken outbound — most founders jump straight to messaging when the real issue is upstream (targeting, subject line, deliverability).

"First, I'll make sure that they're contacting the right person. Second, I'll make sure that they're contacting the right companies. Third, I'll make sure that their subject lines are good. And then, only then, will I actually start looking at their messaging." 00:09:09

Persistence and Speed Win Deals — "Time Kills Deals"

Founders should follow up multiple times and respond instantly once a prospect engages, since delay is one of the most common and costly mistakes.

"If you get a reply, you should be like a heat seeking missile and that nothing is going to get between you and getting onto their calendar." 00:10:06 "Every founder will at least once experience the very painful lesson that time kills deals." 00:10:06

Customers Are the Best Copywriters

The best messaging doesn't come from internal brainstorming but directly from customer language and stated reasons for buying.

"Your customers are always going to write better copy than you do." 00:11:33 "Ask them the single thing they got them to buy, and then use their phrasing in future messages." 00:11:33

Founder-Led Sales Is a Compounding Advantage, Not a Temporary Chore

Gilbert frames outbound grind as building an asset — deep customer pattern recognition that no hired salesperson or agency can replicate.

"No salesperson or agency will ever be able to learn about your customers the way that you can. Your outbound will only get easier over time." 00:12:03

2. Contrarian Perspectives

A "No" Is a Valuable, Not Wasted, Outcome

Most founders treat rejections as failures to be minimized. Gilbert argues that explicit no's are data that actively improve future targeting, and breakup emails engineered to elicit "no" are a deliberate tactic, not a last resort.

"A real no is actually very useful to you. In aggregate, the many no's improve who you target in the future." 00:10:06

Weird, Less Descriptive Subject Lines Beat Clear, Informative Ones

Conventional sales advice says be clear and descriptive. Gilbert's real-world A/B result contradicts this directly.

"The subject line, broken agents, performed a lot better than the more descriptive but less interesting, better agents for every workflow." 00:07:13

Low-Pressure "Breakup" Messages Generate Higher Reply Rates Than Persistent Asks

Rather than escalating urgency, deliberately lowering the pressure (implying you'll stop bothering them) produces better response rates — the opposite of typical sales instinct to push harder.

"Reply rates I find are much higher on these breakup emails because it makes them really low pressure for them to say no." 00:10:06

Sales Tools Like LinkedIn Sales Navigator Actively Mislead Founders

Popular list-building tools are assumed to be reliable filters, but Gilbert points out they systematically surface the wrong companies, requiring manual verification that most founders skip.

"If you search for tech companies in LinkedIn Sales Navigator, you're often going to get a bunch of IT implementation consultancies." 00:02:57

Founders Should Distrust Feedback From Friends, Advisors, and Co-founders on Messaging

There's an implicit assumption that internal stakeholders (co-founders, advisors) are useful sounding boards for sales copy. Gilbert dismisses this entirely in favor of a single source of truth.

"The best feedback on your messaging always comes from your customer, not a friend, not an advisor, and not your co-founder." 00:11:03

3. Companies Identified

Aptin — YC company (S24 batch). Cited as the source of a model outbound email that exemplifies best practice: informal tone, credibility via past experience (founder previously worked as a software engineer at Tesla), personalization, and a clear low-friction call to action.

"It's from the founder of Aptin, which is a YC company in the S24 batch... I used to be a software engineer at Tesla. We got crazy good at using SMS to convert the people who visited our website into car buyers." 00:05:48

OneSchema — Christina Gilbert's own company, referenced as the source of her founder-led sales track record.

"As the founder of my company, OneSchema, I personally generated and closed millions of dollars in revenue through founder-led sales." 00:00:08

Tesla — Mentioned as the prior employer referenced in the Aptin founder's email to establish credibility with the prospect.

"I used to be a software engineer at Tesla." 00:06:17

4. People Identified

Christina Gilbert — Founder of OneSchema and visiting partner at YC. Identified as an authority on outbound sales based on personally closing millions in revenue through founder-led sales and coaching hundreds of YC companies on their outbound strategy.

"As a visiting partner at YC, I've helped hundreds of YC companies improve their outbound." 00:00:08

Sumir (referenced as founder of Aptin) — Praised for writing what Gilbert considers an exemplary outbound email: informal, credibility-driven, personalized, and action-oriented, with almost no product explanation.

"The email also feels personalized to Sumir's company by mentioning that he noticed on their website that they collect phone numbers in the signup process." 00:06:46

5. Operating Insights

Build a Repeatable Diagnostic Funnel for Sales Debugging

Rather than guessing at what's broken, Gilbert applies a strict, ordered checklist (right person → right company → subject line → messaging → materials → deliverability) before concluding there's a product-market fit problem. This turns outbound debugging into an engineering-style process rather than trial-and-error.

"If you go through all six of these areas and they all seem to be reasonable and you're still getting zero replies, this often might be indicative of a deeper product market fit issue." 00:09:09

Treat Outbound as a Scheduled, Measurable Operating Cadence

Gilbert recommends founders pre-commit to concrete daily quotas (messages per day, time per message, exact send times) and put it on the calendar like any other operating metric, using a co-founder as an accountability mechanism if needed.

"The number one difference between founders who actually succeed with outbound and founders who don't is actually following through on the activity that they commit to." 00:11:03

Reverse-Engineer Ideal Customer Profile From Closed Deals, Not Assumptions

Instead of guessing at buyer personas, look backward at who actually pushed existing deals to close and who signed/paid, then pattern-match new prospects against those exact profiles.

"Look at the customers that you already have. Then look at the sales process. Who is the person who is pushing the last deal to close? Who actually signed the contract? Who is the person who paid?" 00:02:02

Mine the First Sales Call for Message Validation

Ask every new customer what specifically got their attention in your outreach — this simultaneously validates your copy and opens a discovery conversation about their pain points.

"One of the first questions I like to ask is, what got your attention about my message?... It also gets them open-endedly talking about their problems, which is exactly what you want in a first call anyway." 00:11:33

6. Overlooked Insights

Growth Inflection Points Are a Universal, Underused Targeting Signal

Buried in the targeting discussion is a generalizable principle: many B2B products have a specific company-size "crossing point" where need emerges almost mechanically (not gradually), making headcount/growth stage a far higher-signal filter than industry or title alone. Gilbert only gives one example (compensation bands at ~100 employees), but the implication — that founders should identify their own numeric inflection threshold — is a much more rigorous and underused segmentation technique than most outbound advice offers.

"So when they're crossing somewhere in that 100-employee range, that's a great intent signal that they need your product." 00:03:56

The First 20-30 Characters of Email Body Function as a Second Subject Line

This is mentioned in a single sentence but has outsized tactical importance: because Gmail previews truncate the email body, founders optimizing only the subject line are missing half of the "first impression" surface area that determines opens and replies — an easy, high-leverage fix most outbound guidance ignores entirely.

"You should also pay attention to the first 20 to 30 characters of the body of your email because that's what shows up in the Gmail preview." 00:07:13