Outbound sales 101

Celine Wee
3 min readDec 27, 2023

I admire excellent craft. And by craft — that includes a really good B2B outbound email landing in my work email inbox. For this post, we’ll park the emails we get as consumers, and focus on B2B sales.

Having crafted and sent cold emails to potential customers while in Stripe sales, I have enjoyed being on the “other side” e.g., receiving emails instead, vs wracking my brain trying to invent creative hooks. Today I’ll cover:

1/ Common definitions in outbound sales

2/ What works (a buyer’s perspective)

3/ Further reading and resources

1/ Common Definitions

  • Outbound: The process in which a salesperson/sales representative reaches out to potential customers/buyers. They can do this via channels like emails, cold calls, Linkedin messages.
  • Prospect: Potential customer/buyer. Prospecting is the process of reaching out to prospects to sell a product.
  • Sales Development: Builds sales pipeline by finding prospects. Helps to source, and qualify the deal. Does not close the deal.
Photo by Austin Distel on Unsplash

2/ What works (a buyer’s perspective)

I don’t speak for all buyers, but want to praise some great outbound content I’ve seen in the last ~two years. I’ve replied to emails which I find a good effort, and tried to forward them if possible.

Know your buyer profile and make it clear in the email. Sometimes I have received an email, and want to forward it internally, but the email wasn’t clear about which team might use the product. In contrast, I’ve had colleagues forward me emails that were meant for my team.

Shorter emails. Hubspot suggested 50–125 words. This is challenging given tailored content is also important, so it’s a fine balance to strike.

A persistent cadence. I was taught to do at least 3–5 “touches” (outreaches). While I don’t have the data to which what gets the highest open rate or engagement (there’s tools like Salesloft which track this), repetition helps.

Speed matters. Reply fast to someone who just got back to a cold email!! That has just become a warm-ish prospect. It’s a pity when I’ve reached back out for more information, and then did not hear back for while.

Hit or miss (depending on buyer, tread cautiously)

This section are on tools that could be a hit or miss.

  • Pictures: An eye catching / seasonal / funny meme that asks the receiver to take action. There’s a risk — some receivers might find it cheesy or annoying, but I personally think it’s fun touch. Note that images might bet filtered as spam or blocked.
  • Video clips (via Linkedin): While I haven’t received a video clip and am generally cautious about clicking links, it sounds like a solid approach.
  • Cold calling: My hunch is that effectiveness widely differs by industry/buyer profile. I am in the skeptical of cold calling camp.

The Harvard Business Review reported cold calling is ineffective 90% of the time, and more recent research shows that less than 2% of cold calls actually result in a meeting. Assuming a 0.3% appointment-booking rate and a 20% win rate, it would take 6,264 cold calls to make just four sales. — Source

However, to quote Salesforce “How effective is cold calling? Research shows cold calling rarely leads to conversions, but cold calls provide immediate feedback, are cost-effective, and are harder to ignore than emails.” It’ll probably remain a large part of the sales cycle for most B2B sales reps.

3/ Further reading and resources

I’ll be the first to admit that I did sales at a time where inbound leads were plentiful, so outbounding was less existential. However it’s given me an appreciation for how hard it is to create great outbound content. There’s alot of sales content on the internet, and I’ll link to the ones I’ve found the most helpful so far.

  • For some fun content I recommend: @Corporatebro on insta — look out for the segments on “cold calls” — hilarious.
  • For serious content I recommend: Skip Miller’s book on outbounding — he’s the original. Hubspot also has a great summary list, and Salesforce has a whole academy of sales content.



Celine Wee

Opinions are my own: a collection of Go To Market, Payments, Biz Ops learnings across Stripe, Coinbase, Twitter. I also write @celinewee.substack.com