B2B Outbound Sales Strategies with Ryan O’Donnell

January Ventures
5 min readMay 17, 2021


We were recently joined by Ryan O’Donnell, Co-Founder and CEO of Replyify and SellHack, two tech platforms used by thousands of companies, both large and small, for generating a consistent sales pipeline. SellHack is a Chrome browser extension to build targeted prospect lists and Replyify automatically sends out your cold emails so you’ll never forget to follow up again.

Ryan is a growth marketer obsessed with helping sales professionals and business owners sell like a robot while still sounding like a human. He implements the software platforms he’s built to consistently generate over $1M in revenue.

Ryan spoke with our portfolio founders about B2B outbound sales strategies, specifically touching on approaches to find the best prospect segments, write cold emails that get opens and responses, and use automation to generate consistent leads.

Here are some of the key takeaways from the event:

There are three different ways to grow your business:

  • Increase your average order value
  • Increase number of transactions
  • Increase the number of customers — use B2B sales strategies

How to build your prospect list

Do the very manual exercise: Look at your last 10 customers. Copy them into an excel spreadsheet, and put columns in for job title, industry, location, keywords.

If you don’t have customers, find your competitor's customers.

Take a data-driven approach to identifying your customer personas — you can repeat this exercise every six months to make sure you know your customers, especially since new clients coming in might have a different persona than you realize.

Stalk your prospects (legally). Fish where the fish are. Most of the people you’re reaching out to will be on LinkedIn. Get a paid Linkedin account — sales navigator is ideal because you can get much more search criteria. Based on your spreadsheet, look for clusters or patterns. For example: titles, company sizes, locations, etc. Each of these clusters becomes a different segment. Filter your search and LinkedIn search results will give you a bunch of data.

SellHack is a Chrome extension. It takes your search result from LinkedIn and lets you add the contacts to a list up to 20 at a time. They do real-time lookups to find email addresses.

Find prospects while you sleep

You can run an “advanced search” on LinkedIn, save your search results and new prospects will be sent to your inbox — usually, they are people who just got a new job or got promoted.

Most effective way to reach out to prospects

LinkedIn connection requests, emails, phone calls, etc?

If you can set up emails in an automated way that doesn’t sound spammy, it can all happen in the background.

Cold email campaign best practices

You can’t cold email with MailChimp — they’re built through your opt-in and typically end up in the promotions folder.

One-to-one emails get read at a much higher rate — personalized, short, sweet emails get replies.

  • Personalize emails with variables
  • Use concise subject lines — and try ‘variables’ to add their name to the subject line
  • Don’t throw the kitchen sink into your email — 3–5 sentences max per email
  • Send 5–10 emails over 21–45 days — send out these emails at staggered times, so a group of people won’t be blasted at the same time. Varying the times signal they aren’t automated
  • Never send ‘naked’ emails with something weak, i.e. “checking in to see”
  • Limit images and links
  • Give a clear, low commitment call to action

How to write your email campaign

  1. Write your intro email and two follow up emails
  2. Take your email and pretend you’re the one getting it — would you read this email? Typically, you need to remove a lot of the content and split it up into follow-up emails
  3. Be aware of what your prospects will respond to — use data social proof (work with your competitors), discounts, and knowledge/content. Each email can focus on different elements — Replyify is a tool to help you do this.

Emails with Replyify don’t look automated

  • Emails go out directly from your email account
  • They include unsubscribe links — you need to give contacts a way to remove themselves. For the first email in particular, make sure the unsubscribe is there.
  • If you get your emails marked as spam, it can hurt your delivery rate. This is mostly text-based — make sure there aren’t too many links.

Additional tips

  1. Set up a separate email account
  • Set up an alternative email address, on a separate domain.
  • At some point in the future, you’ll want to use this email address. Give it time to warm up. Warm up your email address at a lower volume, and eventually send out all your emails on your secondary domain.
  1. Automatically book meetings — Use a tool like Calendly
  2. Excel during the meeting — Create a demo playbook, pitching & closing document, and objection handling document
  3. Utilize email automation for other tasks
  • Expand your prospect segments — test out whether other personas might be interested
  • Test new product ideas
  • Make an email course (can be delivered through Replyify)

Q&A with Ryan

Q: What are the differences between Reply.io, Outreach, and Replyify?

Fundamentally, they do the same thing. You set up an email sequence, add contacts, and let them go out. Outreach is more focused on enterprise.

Email deliverability will mostly fall on the domain. But some of it also falls on the provider, like Replyify.

Q: How does email warm-up work?

If there’s a huge difference in your email volume, you can get flagged. You can end up on a list and will get watched. So you want to step into your volume, otherwise, your email can get shut off if you eclipse the limit.

Replyify has a warm-up account feature to ramp up volume slowly over 30–60 days.

Q: How do LinkedIn automations work?

You have to manually process the LinkedIn list building. They’ve gotten strict over this in the past few years.

Q: Cold outreach via text?

The more channels you can reach out with the better.

If you have an SMS provider, you can use their webhook and pop it into the Replyify sequence.

No downside to adding another channel as long as you have time to take the meetings.



January Ventures

January Ventures (previously known as Jane VC) invests early and opens doors for the visionary founders of the future.