Startup Sales: Everything You Need to Know About Building Your First Sales Team

Startup founders are stretched thinly like silly putty. 

Between hiring, training, and helping new employees excel, iterating on customer feedback, building brand awareness, et al., there are hundreds of activities you can engage in on a daily basis. But the one thing you must think about is sales.

Without sales, your startup dies.

Yet, sales is all too often a dirty word. One reason for this is because early sales managers repeatedly make avoidable mistakes on the journey to go-to-market fit. They overpromise and underdeliver.

They go for the sale without caring about what the customer needs in the first place.

They get salesy.

It doesn’t have to be that way. Below, I share common pitfalls and techniques in four fundamental areas of startup sales. We’ll hit:

• Your first sales playbook
• Sales hiring: mistakes and must-dos
• The importance of sales methodology and why you can’t wing it
• Finding the right sales ops balance

In each section, I’ll also aim to give advice about how to repurpose first version of these assets as you evolve your go-to-market strategy because with limited resources, you should make key assets, like sales playbooks, fungible.

I wrote this because sales isn’t a magic switch you turn. SaaS founders and operators need help structuring and understanding the importance of sales basics. 

But it is also a lot of text. So feel free to look around and jump to the sections that are most relevant to your team. Here’s a summary on the content to make it easy to jump to the part you’re most interested in:

Table of Contents

• Your first sales playbook
  • Your second sales playbook
• Sales hiring pitfalls and must-dos
  • Characteristics of high performers
• Sales methodology and why you can’t wing it
  • Which sales methodology is right for me
  • Coach regularly
• The sales ops balance

Or jump right into it!

Your first sales playbook

Your startup sales playbook is your evergreen guide to securing happy, paying customers. It’s a collection of your processes and practices that help you achieve your sales targets and continually improve your sales organization.

But where do you start when you want to create your first one?

Your earliest customers will shape your thinking, your next few moves, and even your cash flow. Without knowing it, you’ve started to lay the groundwork for your sales playbook and your go-to-market engine.

Here’s what I mean…

Remember the first customer you closed? How after that payment was processed or that service order was signed, you set your sights on cloning that customer. 

“Go get X-number more of Y-type customer,” right? 

Nod your head if you’re guilty of saying or thinking this — for many startup sales organizations this is where strategy starts and ends.

For many sales organizations “Go get more X-type customers” is where sales strategy starts and ends.

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Because you’re trying to figure out how to replicate and quicken your successes, it can be tempting to build your sales playbook around your first customer or an early customer that contributes significant revenue and product feedback. Or a customer that simply makes you feel good.

Beware of this bias though. Spend time striking the delicate balance of understanding who you are and who you want to be. Next, start to write this down — along with the processes and practices you need to execute consistently to achieve your vision. And voilà, you’re on your way to an early sales playbook that can focus and strengthen your commercial operations.

Here are a few prompts to help you get started on the why (which you’ll want to do before interviewing sales candidates — the good ones will ask these kinds of questions):

• What does the buying experience feel like for your customers? What is it like to be on the receiving end of sales messaging and calls?
• How do you expect your individual operators to behave? What do you want your sales culture to be like (or not be like?)
• What motivates your sales team?

And now, some on the how and the who:

• How is sales involved in that process? What sales model is right for your customer’s buying experience? What sales model is right to help you achieve your desired outcomes?
• What does your sales team need to know about the industry to be a credible and successful advocate for your product and for prospective buyers?
• What problem do you solve for which kinds of buyers? (note: this is the beginning of your ideal customer profile (ICP) and buyer persona definitions)
• How do you get a conversation started with those key people?
• What are the general motions of a sales cycle?
• What can go wrong and what should you be on the lookout for?
• Key wins and why they matter

A thorough introspection, even if incomplete, makes it easy for future hires to succeed. Don’t expect a new hire in sales (or any domain, really) to come in and solve your puzzles and problems. I see people make this mistake for VP, C-level, roles, so why would you set this precedent and make this mistake for individual contributors or even junior salespeople?

This exercise also gives you the opportunity to ensure that from the get-go, your commercial team is operating in a way that is aligned with how you want to run the business — instead of allowing new hires to apply old or inappropriate sales methodologies that will burn leads and shape customer opinions.

Your second sales playbook

A perfectly crisp sales playbook may feel unattainable because like most startup operations, you’re learning about your ICP and your messaging as you sell. In fact, when I asked Khris Fenton, Director of Sales Enablement and Operations at WealthEngine for his definition of a sales playbook, he laughed and said, “That thing I want to do but simultaneously don’t think I’ll ever complete.” 

Of course, no one wants a shoddy or incomplete sales playbook. Your go-to-market strategy and how you articulate it to your sales team needs serious and regular fine-tuning (and at some point, a full-time or even team of certified, top-notch mechanics).

If you’ve spent time massaging a first version of what I’ve described above, my next advice is three-fold:

• Get crisp without overengineering
• Maintain a narrative
• Begin building sales tools

As your understanding of your buyers matures, you should get as specific as you can without building in details that will quickly be forgotten or dated. Keep in mind that the best and most motivated salespeople will be curious for industry and product information in order to sell better, faster. More concrete information on the industry, guidance on messaging, and customer success stories will help future hires ramp faster.

Your playbook can evolve to include specific detail on:

• current trends and common language in the industry (even acronym definitions)
• defined key differentiators about your product and company
• pain to probe for
• required reading and training materials
• messaging standards and/or sample messaging (email templates, proposal advice, etc.)
• product and content marketing assets for different sales touchpoints

To me, a healthy startup sales playbook has consistent material that is consumed daily and iterated on monthly. I find that a lot of the battlecards, buyer personas, and templates are superfluous exercises to show commercial progress. While you should of course put the energy into giving smart guidance, beware of growth techniques or candidates that sell a magic pill.

The other key indicator of a useful sales playbook is its narrative. As your content and sales tools begin to grow, it can be challenging to weave together the core components in a way that is consistent. That’s why I suggest spending significant time on the why of your sales organization. If your sales team has a way to evaluate their own behavior and customer interactions against the organization’s expectations and standard operating procedures, they’ll be better situated to course correct with available resources.

Finally, you’ll begin to bake in some sales templates and tools. I’ll talk more about sales ops later on, but my guidance is to work on building your first sales tools quickly and one at a time. It will likely happen organically — a new hire will ask questions like ‘how can I overcome an objection about a missing or inadequate feature’? So, you (or likely your first sales manager) will begin to create assets like this:

Which can get even further fleshed out into guidance/assets like this:

Sales hiring pitfalls and must-dos

Now that you have a sales playbook with concrete answers to questions sales candidates will inevitably ask, you’re ready to begin hiring. 

Whether you have help from an HR department or you’re a lone recruiter/sales manager/quota-carrying badass, I encourage you to follow a structured process. This will help you combat the feeling of being ‘sold’ during the interview process and ensure you’re evaluating characteristics of high performers.

This is the process I use to hire a full-time Account Executive at ChartMogul:

1. Initial phone screen: the purpose of this 15-30 minute interview is to get on the same page on three things — competencies, culture, and compensation.
2. Hiring manager video interview: this is the deep dive. This is where I’m looking for core competencies. In this interview, I ask questions to assess sales experience, skills, and methodology. Depending on the role, I look for 6-9 characteristics of high performers (some examples on this below). 
3. Sales skills evaluation: this is the practical exercise. It can also vary by role (e.g. a writing prompt, a discovery role play, a product demo, or a territory plan), but should be hands-on with some required prep work. I also like to use this exercise to assess self-awareness and coachability.
4. (Optional) Peer interview: this can be useful if you’re competing in a tight talent market and want to give the candidate a different perspective. It’s especially helpful if all other interviews have been conducted by the hiring manager.
5. CEO interview: this depends on the size/structure of the organization.
6. Reference checks: I like to use reference checks to understand how best to set up a prospective employee for success.

Some organizations use scorecards and ATS systems like Recruitee to track interviewer feedback and candidate progress, but don’t apply unnecessary structure.

Characteristics of high performers

Ready to schedule those interviews? Not so fast. 

Before you talk to the first candidate, earmark the key characteristics you expect candidates to showcase during the application process. In addition to evaluating startup sales experience and product knowledge, candidates should exhibit specific characteristics that will help them win over your buyers and excel long term. This will make sure you hire a great fit candidate — and help you avoid the “shiny object” syndrome where you get excited about a candidate because of a great logo on her resume.

The average sales organization salesperson turnover rate is now 34%, with “involuntary turnover up nearly two-thirds of that number.” The same research suggests that one in ten companies experience turnover rates above 55%. The new average time for reps to ramp to productivity has reached 5.3 months. On average, only 67% of reps are making quota, down from 74% in 2012. No matter how you spin it, the data reflects an unfortunate trend.

Anthony Chaine

And for next-level startup sales hiring, list out those characteristics. Some of those characteristics depend on your sales model and your industry. You can pinpoint those characteristics by reflecting on sales methodology (more on that later).

Here’s what I mean:

This is a sample list of characteristics we evaluate during our AE hiring process:

• Business acumen
• Consistent execution
• Storytelling
• Likeability
• Offers a unique perspective
• Drives two-way communication
• Credible as an expert in SaaS
• Comfortable discussing money
• Can pressure the customer

By itself, it’s a fine checklist. But have you ever had that nagging feeling after conducting an interview? Maybe something bothered you but you just can’t put your finger on it? By defining those competencies and providing evaluation guidelines, you can make sure that you, or your HR team, aren’t checking those boxes simply to get a body in the door.

It takes ~50 days on average to hire a sales professional. Don’t rush it. Salespeople are skilled practitioners of selling themselves too.

One of the essential pieces you have to get before you’re ready to hire is to define the “why” of your sales organization:

The best salespeople want to believe in what they are selling. And even more so, they want to believe in the business they are building by selling your product/service.

So if you need to bring on the right salespeople NOW, show them how you’re making a difference why they should drop everything to get on board and be part of your mission.

Amy Volas

Here is an example of how we evaluate one competency in the interview process. You can ask these questions in a video interview or even to a candidate’s supplied reference:

It’s possible, that you find a candidate that you’re ready to hire, but who does not excel at every targeted competency. With a structured interviewing process like this, you can identify areas of potential concern and proactively work them into your onboarding and management strategy. If there is doubt, though, stop and close out the process.

There is a lot of competing advice about whether you should hire a sales candidate with nearly identical skills and experience and/or an existing network of contacts. For example, if you sell healthcare wearables to hospices and palliative care organizations in the U.S., should you only hire from that talent pool?

In truth, I’ve seen this formula take off and also fail spectacularly. If you have a particularly niche product or require relationships with larger channel partners (like Salesforce, Oracle, Microsoft, Atlassian, etc.) it might make sense to hire from the same pool, but it’s also harder and more expensive.

For most SaaS companies, I would recommend hiring salespeople who have worked similar deal sizes and sales cycle lengths. It improves ramp time and helps them stay engaged.

The best practice for SaaS companies is to hire salespeople who have worked similar deal sizes and sales cycle lengths. It improves ramp time and helps them stay engaged.

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For example, if I hire someone that was closing deals on a 15-30 day sales cycle and my sales cycles are 6-9 months, I run the risk of that person a) not being successful and b) getting bored/being a retention risk.

It can be a very expensive and painful mistake to make. Hopefully, by now I’ve debunked the idea that anyone can sell at your startup. Like any critical role, executing a planned hiring process will help you hire and retain top talent.

For further resources about how to structure sales compensation plans, I recommend: SAAS Sales Compensation Simplified

Startup sales methodology and why you can’t wing it

Stick around a group of battle-tested sellers long enough and someone is sure to tell you how their blue sheet helped them nail that RFP process last quarter.

Miller Heiman, Sander, SPIN, Challenger, MEDDIC, SNAP. There’s no shortage of options if you’re on the hunt for a sales methodology. 

Unlike a sales process, which focuses on defining the steps or stages on the path to purchase, a sales methodology offers a framework for how sales reps can approach each of those stages to win the deal

Jacco van der Kooij

Your sales methodology defines your approach to the buyer-seller relationship and how your team solves prospect problems. A defined sales methodology is the foundation of your sales organization — and should come before your sales model or process. 

For startups, applying this much structure may seem counterintuitive or even like a waste of critical resources. Perhaps this is because, as Kooij goes on: 

Most of the most popular sales methodologies are trademarked and were created by sales consultants and trainers, who wanted to define their own signature approach. Unfortunately, this means many of the methodologies you’ve heard of are really products being sold to you.

Here’s why it’s so important though.

Your startup sales methodology grounds your decision-making process. In sales (and startups for that matter), every day, every call is filled with countless decisions. How should I frame this? What should I highlight in my demo? How will the customer respond? What are the customers priorities and how can I communicate effectively? When is the right time to follow up and what should I say?

Process can help you answer some of these questions but methodology gets to the heart of the matter. A well-defined sales methodology brings cohesion to the sales process and arms your sales team with a compass for what to do when a new decision or question arises to which there is not an obvious answer. If done well, it can help eliminate that paralyzing feeling of what should I do next or what if I do or say the wrong thing.

Which sales methodology is right for me?

It depends.

To start, have a serious think about what the selling and buying experience was like for your first few customers. You want to employ a refined methodology that is most aligned with your prospective customers.

• When and how were they aware of their problem/opportunity?
• What steps did they take to learn about and evaluate solutions?
• How do they want to engage with your team? What are their expectations about the sales process?

From there, do some research. And be sure to put that research into context. Know that the Challenger Sales model, for example, is about building consensus with various stakeholders in a large enterprise sale, so if you are hunting mice, your methodology shouldn’t involve educating the customer about their problem.

Don’t feel like you have to latch onto every piece of advice within a methodology, but as your decision will be the foundation for your sales organization, it’s important not to waver or to introduce frequent changes.

Coach regularly

Too many startups expect salespeople to be immediate and consistent star performers. One constant, regardless of what industry your startup is in, though, is change. As your sales playbook, markets, and products evolve, you should expect to invest regularly in the development of your sales reps.

Andy Farquharson

Document and exercise your methodology. One way to make sure your sales methodology runs deep is to conduct regular role-playing and coaching exercises. Our team chooses a tough customer call each week and workshops key inflection points. It’s a standing commitment but well worth the investment — because we know practice makes sales practitioners better.

The sales ops balance

By now I’ve asked you to document an entire playbook, your sales hiring practices, and a sales framework and we haven’t even introduced process or technology. Who manages all of this?

There’s a reason startup sales and revenue ops are so prevalent in most B2B sales organizations — it’s a lot of moving parts. 

Your sales team is responsible for bringing revenue into your company. Your sales operations team helps them do it faster, better, and with a lot less hassle. It’s a crucial part of your sales organization.

Steli Efti

Sales ops can be a catch-all for:

1. Sales stack management — CRM and sales tool administration
2. Sales strategy and process improvement
3. Sales reporting and forecasting
4. Sales training and curriculum development

Unfortunately, sales ops is all too often an excuse for management to ask questions and validate hypotheses about sales and marketing performance.

“Can you show me a report of converted leads from the SaaStock conference?” Reporting and quantitative analysis are necessary for team and individual performance improvement. Beware, though, of investing your limited resources in CRM dashboard perfection when your processes are evolving.

Really sales ops is responsible for managing how your organization systematically improves how the buyer-seller relationship works.

One way to implement a regular rhythm of sales improvement is with a defined change management process. If you’re triaging Slack messages and sticky notes from your team with requests like “can we add a new field to track buyer persona?” start by putting all of those requests and suggestions in one place.

Here’s what I mean:

You can use a board like this to identify and prioritize common challenges in your sales organization. You can also use it to iterate on your training materials. As your sales organization matures in tools and processes, you can feed “completed” items on your change management board back into your sales playbook so that new hires have all of the details on how leads are assigned.

It’s okay if non-priority items sit — as long as you’re growing and improving the sales organization in a sustainable way that makes sense for the business. You’d be surprised how many emergent requests do not impact you or your team’s ability to sell because like most other areas of SaaS, there is no silver bullet CRM for sales productivity and higher win rates.

A solid foundation for startup sales success

No startup can survive without selling.

But that doesn’t mean the early-stage scrappy founder-does-it-all-type of selling will work as your company matures.

On the contrary, one of your essential focus areas as a founder is to lay down the foundation for scaling your commercial team.

In this post, I tried to collect the essential elements of such a foundation:

• Building a sales playbook that collects essential processes and tools
• Successful startup sales hiring
• Picking a sales methodology that supports your organization
• Getting the right balance in sales ops

But once you’ve developed (and documented) your initial thinking about those, it doesn’t mean your job is done.

Just like you constantly iterate on your product, so you should look for opportunities to improve your sales operations. A big part of the inspiration for those improvements will come just as your team goes out and talks to customers. But it is essential that you develop a process for recording, analyzing, and acting on the insight you get from selling.

My final piece of advice is — don’t be scared. I know selling sounds intimidating, especially to those who come from a technical background, but just like with building a product and/or a company, you tend to develop an appetite for it once you start doing it.