Field Guide
ToolsButton Text
Startup hiring

As companies scale, founders need to offload sales to a salesperson. But founders MUST stay involved with users. Scale more effectively with these NEW actionable tips, including a downloadable Salesforce package.

Tab 1
Tab 2
Tab 3
  • TL;DR
  • Since design partner installs are focused on product usage and feedback before you can contemplate converting them to paying customers, it's impossible to give a sales hire a quota to hit because you haven't priced your product yet. We advise founders to look for a sales hire who has the skill set and functions more like a revenue-generating product manager.
  • Many sales candidates will only be comfortable in a role where they have a playbook they can learn, sales enablement to bolster that learning, warm leads to start working, and a clearly defined quota they have a decent chance to hit if they work hard. This is not the environment of a Seed or Series A startup in the design partner phase.
  • The future state allows the prospect to step into the hypothetical where their current problems and the negative consequences they cause have been solved. These potential positive business outcomes also need to be quantifiable, and you’ll need to press for those numbers to make sure it’s something the business actually cares about. What gets measured gets managed!
  • Companies similar to Databricks, Segment, MongoDB, Sumo Logic, and AppDynamics would expect a commercial/mid-market sales rep to hit a quota between $500K–$1M annually, and would cost the business $160K-$240K in on target earnings (OTE) between base and commission. This would produce a sales yield between 3 and 4. The sales yield expectations would be similar for enterprise sales reps.
  • We advise founders who need to scale their sales teams to think about doing so in pods of sales reps, solutions engineers, SDR/BDR, or support engineers.

If you've been reading all the Sales in a Modern GTM articles in our Field Guide, you and your team are now four quarters (one year!) in and have successfully done the following: 


  • Completed the GTM framework exercise to segment your markets into innovators, design partners, and early adopters
  • Interviewed 50+ innovators, informing your first product roadmap
  • Received commitments from 10–15 innovators to become design partners 
  • Installed your beta product with five–10 design partners for hands-on feedback and iteration
  • Defined your first sales process to start qualifying which design partners have the highest propensity to buy 
  • Converted three to five of your design partners to paying customers 


During the next six months, you and your team will systematize your sales process by installing Salesforce and creating a sales wiki, hire your first sales leader/rep/pod, and scale your pipeline and net-new customers. This phase usually covers months 12–18 in our timeline. 


Up to this point, we’ve been using an 18-month timeline, but it’s important to call out that it’s not the end of the world if your timeline stretches to 24 months. If you need to spend more time in any of the three phases we’ve outlined (innovators, design partners, early majority) you can factor in a six-month buffer. If you start going beyond 24 months and haven’t hit the milestones for your next fundraising, then it becomes problematic. 



The dreaded Salesforce install 

Just like engineering teams use tools like GitHub as a central repository for all things code, your GTM team needs a similar repository, and that’s where Salesforce comes in. 


Salesforce gets pigeonholed as a tool that only salespeople use, but in reality it functions as your GTM database and a source of truth for everything and anything related to your USER/BUYER journey. Even if you end up using tools like Amplitude, Marketo, Clearbit, Gainsight, or have all these sync to Snowflake, AWS, etc., Salesforce will still be the GTM GUI (graphical user interface) that all non-engineering teams default to. 



What to track in SFDC (Salesforce.com)


Sales process 

The good news here is that we’ve already defined these stages — discovery, scope, validate, negotiate & close — so you can just input those. 


Leads, contacts, and companies

Any prospects and associated companies that you want to pursue, have interacted with, or are currently trialing your product. Paying customers are not included here. 


Opportunities

This is how you’ll track each sales opportunity, and it will include all the details around who you're working with (prospects/company), what you’ve learned about their current state, what products could solve their problem, and where they are in the sales process


Forecast

When you look at your sales opportunities and sales process, you’ll have to make a determination on when they are qualified to forecast for the quarter. This simply means you're X% confident that, based on what you’ve learned, they will buy from you by a specific date, for a certain price. Typically, when a sales opportunity enters "validate" in the sales process, you’re more than 60% confident, and would forecast it as “Best Case” for the quarter. When an opportunity is in the later part of the validate phase and you’re compiling the testing results, you should be 85%+ confident and would forecast that as “Most Likely”. 


Forecasts usually have a breakdown that looks something like this: 

  • Total pipeline across all stages for that quarter: $2M 
  • Pipeline (anything before "validate"): $1.05M
  • Best-case opportunities: $600K 
  • Most likely opportunities: $350K 


If you were to make a call on what you would close that quarter based on the snapshot above (let‘s assume you’re halfway through the quarter), you might tell the board you’ll close at least $650K (all of your most likely deals, and half of your best-case deals). 


During a quarter, you’ll probably start with the majority of opportunities in pipeline, have a bell-curve distribution in the middle of the quarter, and then should have the majority of opportunities in "most likely" by the last month of the quarter. 


Dashboards & reports

Dashboards allow you to see different aspects of your GTM data/progress in real time across teams (marketing, sales, customer success, etc). Reports can be used for individuals, teams, or company-wide either for weekly workflows or quarterly board meetings. 


Here are some examples of stats and questions you should track that your board (and potential investors) will likely want to see as well: 

  • What’s your overall pipeline for the month/quarter/year?
  • What are the conversion percentages between the stages of your sales process?
  • What’s working the best? Where do most opportunities get stuck?
  • What’s your forecast for the quarter across best case and most likely?
  • What’s your average sale price across all opportunities (open and closed/won)?
  • What’s your average time to close deals (number of days)?
  • How many net-new meetings are you/your reps generating per month and quarter?
  • How many opportunities are you/your reps generating per month and quarter?
  • How many new USERS (not paid) are you generating per month and quarter?
  • For the deals you’ve lost, what are the top two reasons for losing them?

The Unusual Ventures Salesforce package 

We’re aware that the majority of founders have never installed Salesforce (SFDC) before. Even if you have, it’s a 40–60-hour process that can require consultants or a lot of trial and error to get right. 


That’s why we created The Unusual Salesforce Package for founders to download and install. This has our recommended configurations for all the features we outlined above, right out of the box. Documentation for installation, setup, and use is included.


This unmanaged package is meant for founders who purchased an SFDC Enterprise license and do not have a current instance of SFDC running with real data in it. Since the Unusual package has custom fields, if you install this on an existing SFDC instance, you run the risk of getting errors in your data. 



‘A revenue-generating product manager’

Founders often ask us when they should bring on their first salesperson and what their profile should be. Whether you’re running a product-led or qualification-led sales process, this tends to occur at the same point in time and the profile you’ll look to recruit with is very similar across companies and products. 

Hire when you’re ready for design partners


When you’re ready to start scheduling installs with design partners, you will probably be ready to recruit your first sales hire to offload managing the sales process. It's at this point when founders such as yourself tend to find themselves overloaded with all the responsibilities across the business. 

Keep in mind, however, that you should never offload interacting with USERS, design partners, and customers. What you do offload is the tremendous amount of work around prospecting, scheduling, running the sales process, keeping SFDC up to date, etc. Anytime there's an interaction with a USER or potential user, especially when product feedback will be discussed, founders need to attend at least 60% of these meetings to always stay close to what the market is saying. If you’ve gone two weeks without talking to a USER or potential user, course correct immediately. 

What should the first sales hire profile be? 

Since design partner installs are focused on product usage and feedback before you can even contemplate converting them to paying customers, it would be impossible to give a sales hire a quota to hit since 1.) that's not your focus at the moment and 2.) your pricing model hasn’t been figured out yet. This is why we advise founders to look for a sales hire who has the skill set and functions more like a revenue-generating product manager


Recommended salesperson attributes:

  • Have had success in sales roles where they are responsible for a quota and closing deals (even though this is secondary at the moment for your startup) 
  • Are comfortable without a sales playbook or sales enablement, and would see creating/owning those as a benefit 
  • Can learn your product, competitors, and market inside-out, almost like a solutions engineer without the deep technical aptitude. Keep in mind that this is not a given with sales reps, since the majority can memorize a qualification and demo script, but rarely have deep knowledge beyond that. 
  • Can listen for feedback on the market, competition, product, pricing, and will tag this in your CRM to discuss with the rest of the GTM team 
  • Can prioritize design partners to target those with the highest probability of first installing, then converting to a paying customer
  • Understand that you need to prioritize adoption first, then revenue, and will work toward those metrics for how they will be measured until you jointly determine what a reasonable quota would be post–design partners. 


Many of the sales hires you’ll interview will only be comfortable in a role where they have a playbook they can learn, sales enablement to bolster that learning, warm leads to start working, and a clearly defined quota they have a decent chance to hit if they work hard. This is not the environment of a Seed or Series A startup during the design partner phase. 


You can use the qualities above as qualifying questions in your sales interview with them, and should also reference the list of sales interview questions we’ve built out in Hiring your first sales leader.

Your first sales pod

The first sales hire or “revenue-generating PM” is the one who helps you pioneer what’s possible in their role and what expectations should be across prospecting, sales process conversion rates, average sale prices, average time to close, etc. 


You’ll also have an early indication of your sales yield. Sales yield is what a sales hire generates in revenue after you subtract their cost to the business. Ideally, you want to hit a sales yield of one ASAP, but will be below that threshold for the first few months. 


For context, companies similar to Databricks, Segment, MongoDB, Sumo Logic, and AppDynamics would expect a commercial/mid-market sales rep to hit a quota between $500K–$1M annually, and would cost the business $160K–$240K in target earnings (OTE) between base and commission. This would produce a sales yield between three and four. The sales yield expectations would be similar for enterprise sales reps. 

Sales wiki


With your first hire, you’ll want to create a sales wiki. This is where all your sales materials and tooling live, including best practices and documentation. You'll standardize on this material as a basis for all sales activity as you expand your team. Examples of items you’ll need in that sales wiki are: 

  • Onboarding documents 
  • A completed copy of your GTM framework 
  • A standard sales deck 
  • Sales messaging for outreach, broken out by use case 
  • A link to SFDC and explanation of how you keep it updated 
  • A breakdown of your sales process and explanation of the gates 
  • A standard list of qualification questions and a pre-meeting planner for how you prefer to capture feedback in meetings with prospects 
  • A pricing sheet for how to size and price potential customers 

What is a good profile for new sales hires?

Once you have all of this documented, and after the first five to 10 customers, you should have a good idea of the repeatable aspects and sales yield, and can now create a “standard” sales role to fill, along with the supporting cast required. These sales reps are focused only on hitting and overachieving their quota by learning your product and sales playbook. 


The sales attributes you’ll want to look for: 

  • Have they shown success at hitting a quota for two to at least three consecutive years? 
  • Have they sold into your market or to your USERS before? 
  • Have they sold a product with a similar ASP (average sale price) and time to close? 
  • Have they had success in a role that required a similar breakdown of inbound/outbound pipeline generation? 
  • Have they worked at a similar-stage company before? 


Then, some of the individual attributes you want to look for are: 

  • Are they driven? 
  • Are they intelligent (measured more in ability to learn than book smarts)? 
  • Are they coachable? 
  • Do they have a genuine interest in the company you’re building? 

Hire one pod at a time

We advise founders who need to scale their sales teams to think about doing so in pods of sales reps, solutions engineers, SDR/BDR, or support engineers. Your specific combination will derive from your learnings with your first sales hire and what your team needs to look like to support your initial customers. For some companies, landing the deals is harder and requires an SE/SA to de-risk and expedite that process. Others might find that their average time to close is relatively quick, but customers need more support post-sales, where support engineers come into play. 

Whatever your combination is, we recommend trying to hire one pod first to support your initial sales hire and see what the sales yield is for that unit after three to four months. If things are working well, and you have the ability to do so, you can hire an entire additional pod, and so on. This allows you to increase your sales capacity and sales productivity quicker than hiring a team rep-by-rep. This approach can dramatically accelerate pipeline and revenue growth, as long as there isn’t a break in the product, process, or pod members that would cause you to pause hiring and triage. 


Differences between commercial, mid-market, and enterprise sales reps

Here are some of the main differences between commercial, mid-market, and enterprise salespeople.



Up-leveling qualification: MEDDPICC

A key aspect of scaling a sales team is being able to speak the same language when qualifying deals and reviewing the team/individual pipeline and forecasts. 


Earlier in our design partner article we talked about using the requirements for the gates in the sales process as qualification tools. Now, we'll dive into the default qualification methodology we use at Unusual that’s powered some of the most high-profile and successful B2B IPOs: MEDDPICC. This stands for Metrics, Economic buyer, Decision criteria, Decision process, Paper process, Identify pain, Champions, Competition.


There’s a chance you may have Googled “sales method” or “sales qualification method” which showed tons of frameworks, all slightly different than the other. In the acronym MEDDPICC, each letter simply represents a piece of information you need about an opportunity to determine if it’s qualified (aka real), and if so, how qualified. By capturing the information required by each of these letters, you will not only have a common language internally for how to talk through and evaluate opportunities, but you will also significantly derisk your sales forecast. 


Before we dive into each letter, a brief disclaimer: truly mastering a MEDDPICC qualification method is hard. You’ll hear many people say they use this method, but only a select few have truly built it into their sales DNA (mostly from the companies I just mentioned). So, our goal here is to get founders conversant in the method and comfortable enough to start trying it out in your calls with potential design partners and customers. 

Breaking down MEDDPICC


Metrics: Quantifiable business benefits that your product provides based on past customer success.

Economic buyer: The individual who has the final say on if your product gets adopted, and can allocate budget to do so. 

Decision criteria: Formal product requirements that the prospect needs, which will be used to judge all competing solutions. 

Decision process 

Prospects process for selecting, evaluating, and purchasing a solution.

Paper process 

Prospects required paperwork (legal, security, new vendor forms, MNDA, etc.) that needs to be completed in order to sign an order form and generate a PO (if required). 

Identify pain 

The technical and business pain that are driving a new product evaluation and compelling reason to change/buy. 

Champion 

The USER who has access and influence over the economic buyer that sells on your behalf, and has a vested interest in your success. 

Competition 

Competitive strengths, weaknesses, and differentiators between your product and the other solutions being evaluated (including the status quo and homegrown solutions). 

Capturing prospect details

An easy way to start capturing this information for each potential design partner or customer is to use a slide like the one shown below (and linked here). This way, when you want to confirm what you’ve learned so far, all the information is in one place to present back to the customer to make sure you understand their situation accurately. 



We’ve also created a simple sheet for questions to ask that map to each letter in the MEDDPICC acronym here. So, if we distribute the letters of MEDDPICC over the sales process we outlined, and focus on when we can uncover the required information it would look like this. 



Depending on how comfortable you are with the method, you might have more of an even distribution of letters between Discovery and Scope, but the most important thing to note is that every letter of the acronym should be populated and verified by the customer before any formal product evaluation occurs when you’re looking to sell any version that isn’t a freemium or OSS available. 


This way, by the time you go into a product evaluation, you already know everything about the opportunity, people involved, competition in the mix, and if your product performs well there should be a high degree of confidence (85%+) that they will close as a design partner or new customer. 


The information you have for each letter will enhance after every customer interaction/meeting, so it each aspect will always be influx, but the earlier you start uncovering this information the quicker you can qualify and opportunity in/out, which drastically improves where you spend your time (i.e. only with qualified accounts that have a high propensity to buy).


Continue to: Nurture a self-serve USER/BUYER journey

TOC
Hiring your first sales leader