Dec 15, 2022 · 1h 8m · news
Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Maggie Hott, Director of Sales at Webflow, shares insights on transition models from PLG to enterprise, hiring strategies, interview methods, and scaling sales operations successfully.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19.2% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 4.1 Guest disagreement 1.4 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:03:15 Dismissal of on-site sales travel
Maggie forcefully rejects the conventional view that sales reps need to travel in-person, insisting that buyers value time over expensive lunches.
Hardest push from Harry ▶ 13:33 Challenging PLG plus traditional sales unit economicsHarry firmly questions the business logic of adding traditional sales reps and customer success onto hundred-dollar-a-month PLG software.
Biggest teaching moment ▶ 31:13 Masterclass on tactical discountingMaggie educates Harry on how to leverage discounts as trade-offs to strictly control close dates and secure contract terms.
Harry holds his own ▶ 25:04 Matching guest framework with host operational processHarry demonstrates deep practical knowledge by matching Maggie's 10-80-10 sales email framework with 20VC's exact episode distribution strategy.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Maggie Hott's Unconventional Career Journey to Webflow | 1 | 2 | 0 | 0 | The interview opens with Maggie sharing her non-traditional career path from Eventbrite to Slack and Webflow. Harry mostly listens and lets her establish her narrative with friendly banter. | |
| Hypergrowth Lessons: Cross-Functional Relationships & Tech Stacks | 3 | 4 | 1 | 1 | Maggie shares operational insights about cross-functional relationships and tech stack scaling. Harry asks structured follow-up questions and relates to email etiquette. | |
| Balancing PLG with Traditional Sales and Enterprise Security | 5 | 5 | 2 | 3 | Harry challenges the economic viability of layering sales teams onto low-priced PLG products. Maggie explains product differentiation, enterprise security needs, and SSO features to correct his perspective. | |
| When is the Right Time to Build an Enterprise Product? | 4 | 4 | 1 | 3 | Harry presses on whether founders must quantify ROI before hiring enterprise sales reps. Maggie clarifies the difference between technical founders and sales-minded founders. | |
| Tactical Outbound Strategy and Webflow's 10-80-10 Outreach Rule | 6 | 5 | 2 | 3 | Maggie explains Webflow's 10-80-10 outbound framework. Harry demonstrates expertise by explaining how 20VC uses that exact same personalization framework for guest outreach and episode distribution. | |
| The Psychology of Discounts, Payment Terms, and Negotiation | 2 | 6 | 1 | 1 | Maggie gives a masterclass on discounting psychology and net payment terms. Harry listens and asks practical questions about standard contract terms. | |
| Structuring the First Sales Hires: Avoid the "Head of Sales" Trap | 5 | 5 | 2 | 3 | Maggie advises against hiring a Head of Sales early. Harry pushes on whether stage or domain experience matters more and cites Jason Lemkin's hiring tactics. | |
| The Sales Candidate Profile and Maggie Hott's Biggest Failure | 3 | 5 | 2 | 4 | Maggie details traits for top sales talent and recounts her biggest career mistake at Slack. Harry challenges her premise about salesperson insecurity and asks probing questions. | |
| Revealing Interview Questions for Discerning Top Sales Talent | 2 | 4 | 1 | 1 | Maggie outlines her favorite interview questions to test accountability. Harry asks clarifying follow-ups in a collaborative tone. | |
| Evaluating Companies: Chasing OTE, Quota, and True Equity Value | 3 | 4 | 1 | 1 | Maggie gives advice for candidates evaluating OTE and equity. Harry validates her insights, agreeing that candidate diligence reveals critical thinking. | |
| Quick-Fire: Timeless Sales Tactics vs. the Death of On-Site Travel | 4 | 3 | 3 | 3 | Maggie forcefully declares on-site travel dead. Harry pushes back by citing opposing views from other sales leaders like Frank Filman who miss in-person selling. | |
| The Parental Workforce Crisis & Designing Effective Motherhood Support | 1 | 3 | 1 | 1 | Maggie advocates for better support for working parents and mothers in tech. Harry asks supportive questions with light humor. | |
| New Leader Execution Mistakes and wrapping up the show | 2 | 3 | 1 | 0 | Maggie shares quick tips on avoiding super repping and praises Clary. Harry closes the interview smoothly. |
Statements from this episode (24)
Slack Delayed Building an Outbound Sales Motion Too Long During Hypergrowth
“I actually helped to build out our very first ever outbound motion at Slack, was the very first person to ever do it and ever do our first, which we called Proactive outreach. Cause outbound was, you know, of course a dirty word back then, but it is so importa…”
Scaling Startups Should Buy Software for Future Growth, Not Present Size
“Build things for scale. And what I mean by this is don't buy the cheapest tool now because it's meant for an SMB. If you know you're scaling and if you know your hyper growth, build something for, you know, buy and build for next year, for the year after, for …”
Early Slack Sales Reps Received Flat Salaries Without Commissions or Quotas
“As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest charter was talk to the customers, was understand what is it That the custome…”
Layering Sales and CS Teams Onto a $100/Month Product Is Non-Viable
“You know what I worry about today though, honestly, is we see a lot of companies who do the PLG model with kind of PLG SMB pricing, but then they layer on traditional sales and that business model does not work. I hate to say it, you know, Harvard grads but cl…”
Overly Generous Self-Serve Tiers Cannibalize Future Enterprise Sales Revenue
“Is they have their, essentially their self-serve or their lower end product cannibalize what could be their future enterprise product. We ran into that at Slack. We run into it at Webflow all the time where there has to be a huge product differentiation outsid…”
Webflow Hosts Websites for 250,000 Daily Active Customers
“For example, at Webflow, we have 250,000 customers every single day hosting their websites on us. It's absolutely massive.”
Founders Must Successfully Sell Their Product Before Hiring Sales Reps
“If you can't be successful as a founder selling your product, how can you ever expect someone else to be successful?”
Startups Need $1M to $2M ARR Before Building Enterprise Sales Teams
“And once you have conquered those things, again, to recap there, The pain, the product market fit, some revenue, maybe one to two million dollars in ARR, as well as sell outside of the friendlies, that's the time that it is to start building an enterprise prod…”
Slack Did Not Build an SDR Team Until 2017
“At Slack is we didn't even start building an SDR team until 2017. So we had been around for almost three years at that point before we've really ever started dialing up this outbound motion.”
Cold Outbound Emails Should Follow a 10-80-10 Personalization Structure
“We call it the 1080 10. So 10% personalization within this email needs to be about, Hey, Harry, I saw you live, you know, in London. Here's some common things that people like you struggle with. You know, I saw you were over in Finland last weekend, or whateve…”
Webflow Closed Its Record $1M+ Deal via Rapid Self-Serve Follow-Up
“We actually just closed the single largest deal the company has ever had over a million dollar TCV by doing this exact method.”
Early-Stage Founders Should Prioritize Securing Customer Logos Over Revenue
“I advise them to not worry too much about the revenue early days. Focus on getting those logos because very few people ever want to be the very first mover and shaker.”
Discounts Should Primarily Be Used to Control Deal Close Dates
“Discounts should be used Very selectively, and the single biggest reason a discount should be used is to control the close date of the deal.”
Software Buyers Do Not Pay on Monthly Schedules in B2B Deals
“No one pays monthly for any software.”
Startups Should Always Hire Sales Representatives in Cohorts
“You should always hire in multiple sets of sellers, not for competition, but because it's actually not, not that much more work to teach people, you know, teach a group of people than to teach one person.”
A Bad Enterprise Sales Hire Can Cost a Startup Up to $1M
“A hiring mistake can cost a company to the tune of one million dollars.”
Asking Sales Candidates to Demo Your Product in Interviews Is a Mistake
“And one of the most common things I think people do quite wrong in their final round is they ask people to demo their product. I think this is one of the absolute worst things that you can do.”
Hott Mistakenly Authorized a $200,000 Customer Discount as a New Slack Manager
“So I gave the authority to approve a 200,000 dollar credit to a customer at Slack that my team was selling into.”
Figma Equity Is Virtually Guaranteed Value Compared to Unknown Startups
“200,000 dollars of equity at Figma is going to be very different than 200,000 dollars at Maybe a small company that doesn't have a good chance of success. And is probably either going to get acquired for a nominal amount or just fizzle out because you know wha…”
Stock Option Grants Are Meaningless Without Knowing Total Outstanding Shares
“People get so fixated on the amount of options that they're getting, but options don't actually mean anything. If you don't know how many options are outstanding Or what the actual value is of those options.”
Frequent On-Site Travel Is No Longer Necessary in Enterprise Sales
“You no longer need to be on-site Every single time you need to meet with a customer. I used to be on the road at least once a week. I was always on the road. And yes, it's so important for relationship building, but it just, it doesn't need to be that way anym…”
$800B in Lost Wages Occurred as Women Exited the Workforce in 2021
“And a pretty horrifying stat is that last year in 20, 21, there was more women that left the workforce than any other time in the last 35 years. Horrible. There was eight hundred billion dollars in lost wages to women that happened in 20, 21.”