Awesome People - Ep 31

Sales, fundraising, outsourcing

Hi founders and fellow VC Friends!

Each week we deliver one awesome person to your inbox. These are the people you need to know—the marketers, sales gurus, engineers, ops wizzes— who give your startup superpowers 🚀. The best part is, everyone is hireable on an interim basis.

Please meet Leonard, your marketing-driven sales and fundraising expert

Leonard was introduced to me by Mike Maples at Floodgate. Most recently Leonard founded Dispatchr, a Floodgate-backed enterprise SaaS startup, where he 4x-ed sales for 3 straight years. His secret? A marketing-driven sales framework he used while managing billion-dollar brands at Clorox and Target. He uses marketing feedback to quickly iterate on sales processes, tactics, and messaging.

Lucky for us, he now helps founders with marketing-driven sales and fundraising. He’s helped multiple startups close seed rounds since Coivd and obtained term sheets for another last week.

For B2B sales, you can work with him on sales sprints, lead gen marketing hacks, establishing a pipeline scoring system, and real-time sales coaching. For fundraising, he can help with fundraising sprints, pitching, qualifying investors, and messaging. 

Fun fact about Leonard, he sang at the White House as a child. It’s probably telling that he hasn’t been invited back 😂.

Need sales or fundraising help? Let me know and I’ll connect you with Leonard

He was gracious enough to share some pro-tips with us here

We’re going 50/50 today 😀. Half sales, half fundraising 📈.  


Don’t hire a full-time salesperson until you’ve gone from 0 > 1

When it comes to B2B sales, avoid hiring salespeople too early — expecting them to figure out how to sell your product.  You know your vision, customer, and market better than anyone. Even if you’ve never sold anything before, you’re still the best person to sell early on for your company. Investigate and define the following:

  • Who are your key customer personas/roles?

  • What part of your product gets your customers’ hearts racing?

  • What channel is the most trusted way of influencing them?

  • What’s the most effective marketing/sales mix?

  • What’s the buying process step-by-step?

Have an experimentation vs efficiency mindset

Fast experimentation over perfection is a key element of early success. Early on in our sales journey at Dispatchr, we focused on brand name go-to-market partners, like Accuweather. We worked on the Accuweather deal for ~6 months. Ultimately, the deal got stuck in legal and never closed. After expending all that energy, we were deflated. We decided to broaden our potential partner list and the next month experimented with a wide range of partners. That month, we found a small hardware partner and closed our first $100k+ deal. Eventually, it became a 7 figure deal.

Hack your first 5 customers in 3 easy steps

  1. Prioritize closing speed vs $ or brand for the first 5 customers. The profile of your first customers may differ from your next 50. It’s tempting to hunt whales day one, but whales take longer to close and usually have more requirements. Prioritize closing speed to get your product into the market and learn fast. Understand the differences in your early customers to determine what a good customer looks like and how to prioritize your sales.

  2. Score your pipeline to accelerate revenue growth. Score and prioritize accounts by variables such as champion enlisted, near term compelling event, and layers of decision making.

  3. Attract fanatical champions early on. These champions are usually motivated by personal factors to see you succeed. We call these folks “Johnny Bravos.” Their motivation is often to be a thought leader within their company or industry. Uncover and feed these motivations. You can invite them to give keynotes or co-author thought pieces. Fanatical champions will generally pull you to close a deal because they see an outsized benefit in getting the deal done.


Work backwards

  • Build an investment memo and have VC friends or other founders give feedback. 

  • For Series Seed, look at what milestones and metrics you need to raise a Series A and work backward to figure out $ and headcount.

  • Pitch funds in this order for the best results:

    1. Priority C funds (not a fit) to hone your pitch

    2. Priority B funds (good fit, but don’t lead rounds) for feedback

    3. Priority A (good fit + lead) to land a term sheet 💪

Here’s a link to an “open source” list of investors created by founders

Run fundraising like enterprise sales

Warning sales lingo below 😂.

  • Turn Marketing Qualified Leads (MQL) into Sales Qualified Leads (SQL). Start by qualifying your MQLs (e.g. check size, sector, thesis) into SQLs (e.g. confirm that they’re actively writing checks).

  • Aggressively manage funnel KPIs. If you’re raising $X, then you need #A term sheets, given B% conversion, with #C intros within D timeframe. 

  • Drive to a “no” quickly. You can always come back later with new news. 

  • Run a drip campaign if you want to fundraise later.

Want an intro to Leonard? Let me know and I’ll make it happen.

FT Gems

Last week Zomato (raised ~$1B), an Indian restaurant guide and food delivery startup, laid off 520 people. They made a fancy layoff list here. Ordinarily, I wouldn’t include a foreign layoff list, but a bunch of you have asked about outsourcing. Maybe this could be an interesting route? I spent WAY too long clicking through their bios and some folks are quite impressive.

As a reminder, here are the fancy layoff lists from Uber, Airbnb, and Samsara.

That’s a wrap! Let me know if you want an intro to Leonard and I’ll connect you via email 😀.

Stay awesome,

Julia Lipton

Founder of Awesome People

Founder of Awesome People Ventures

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