How does the way you think about selling need to change as a company moves from 1-2 sellers to a sales team?

Selling is redefined as the company grows and sales responsibility transfers from the founder to a sales team – as a company expands from one or two sellers to a full sales team, the approach to selling evolves. The company that was used to relying on the owner or CEO begins to rely heavily on the talent and efforts of their first few salespeople taking over. This transition usually results in some automatic growth in sales capacity, but it also requires changes in the organization’s approach to sales. 

Companies need to begin thinking about building a strong sales infrastructure and foundation – to achieve sustained revenue growth, companies should prioritize the development of a robust sales infrastructure. This foundation is essential for driving the consistency needed for sustained revenue growth. To accomplish this, companies should focus on the following key aspects:

• Quality Sales Leadership – a strong sales culture is largely dependent on the quality of your sales leadership. An effective leader will build the necessary sales infrastructure and instill a strong culture to ensure adherence to the established systems and processes. 
• Visibility and Accountability – these elements ensure the necessary processes are followed within the sales infrastructure. They also allow you to hone your processes and contribute to the overall success of the sales team.

What are the four “pillars” that you need to focus on as you scale? 

1. Sales Strategy – this is the starting point for scaling your business. However, a strong sales strategy is more than just your business plans and financial forecasts.
2. Sales Methodology – this refers to the sales motion or how you execute your sales strategy. It involves the tactics and techniques your sales team uses to close deals, and it’s crucial for ensuring consistency within your sales team.
3. Sales Analysis – this involves clearly understanding your current sales performance concerning your goals. It’s about tracking progress, identifying areas for improvement, and making necessary adjustments.
4. Sales Organization – this refers to the structure and culture of your sales team. It involves having the right mix of talent, providing proper coaching, and cultivating an environment that encourages growth and achievement.

Strategy

What do you need to define around targeting and go-to-market strategy before you start to grow your sales team?

Define the specific problems you solve – start by clearly defining the problems your product or service solves. This may seem straightforward, but it’s crucial to be specific. Understanding the exact issues you address will help you communicate your value to potential customers.

Define how you differentiate or uniquely solve the problems – differentiation is key in a competitive marketplace. To stand out in a competitive market, get crystal clear on your unique value proposition and document it in a simple one-pager. Identify the 1-3 core differentiators that set your product or service apart.  

Define your target customers – With your value proposition defined, precisely identify the ideal customer profiles that stand to benefit most. Build detailed buyer personas that map to the specific problems you solve. Outline demographic details like industry, company size, and role, along with their pain points and use cases your solution addresses—document target personas to understand exactly who to engage and how to convey relevance. Well-defined target audiences allow for focused, impactful outreach.

Define your sales goals and targets – the final component of your go-to-market strategy is setting your sales goals and revenue targets for the next 12 months. These goals should be realistic and ambitious while aligning with your overall business objectives. It’s important to base your revenue target on evidence from the past 6-12 months rather than simply choosing arbitrary round numbers. Factor in the growth in your organization, how many opportunities are coming in, how you can influence them, and how you build those targets based on leads coming in from different channels. 

Who in your organization should define this strategy?

The sales strategy is largely directed by the Founder or CEO – as the first salesperson of the company, the Founder is best equipped to understand the customer’s perspective and the value of solving their problems. They are responsible for making the first sales and handling the first objections, which form the basis of the sales strategy. They’re probably the best salesperson the company will ever have. 

The sales strategy needs to be documented – often, the sales strategy is not clearly defined or documented. Documenting the strategy is essential for clarity and consistency. It is also crucial to ensure that components of the strategy are understood at every level of the organization, not just the sales team.

What are the elements of an effective sales strategy?

Narrow down the target market – as companies begin to scale, the instinct is often to widen the description of the target market to increase revenue. However, narrowing down and specifying the target market for successful scaling is often more effective.

Set realistic targets – when setting targets, it’s more effective to consider the number of incoming opportunities and how you can affect them. Evaluate your lead sources and determine how to positively impact each source over the next year. The process should be based on math rather than guesswork. For instance, you may acquire leads through Google AdWords, SEO, or SDRs. Each of these areas should be examined separately to create an attainable objective.

How can you create effective sales messaging?

A strong, specific sales strategy directly leads to effective sales messaging – the more clearly you can identify and understand the problems you solve and how you uniquely solve them, the better chance you have to resonate with your ideal prospects. 

Personalization is key to engagement – your messaging needs to be personalized to get the engagement you want. Sales tactics have changed with the use of automation, which previously allowed for a more generic approach. However, in today’s selling environment, demonstrating a strong understanding of who you’re selling to is necessary to reach your audience effectively. Failure to do so will impair demand generation tactics and impede growth. 

Methodology

What do you need to define around your motion and sales channels?

Companies with Founder-led sales often will need a more sustainable sales process – this is something that you will have to build out as you transition away from a founder-led sales organization so that you have a process that can support a scaling sales team. 

Start with coverage and territories – the first step in creating a robust sales methodology is identifying the right mix of demand-generation activities. Look at your addressable market and define who is responsible for what action and what they will be held accountable for. Understand the roles you need and how to segment for effectiveness. 

Determine how leads from different sources need to be treated differently – for example, there’s a pretty big difference between an inbound lead and an outbound lead. There’s a difference in how they convert and where they are in the buyer’s journey, and as a result, sellers need to have two different presentations for inbound and outbound leads. 

Then, there are three components of the sales process to understand and define: 

• Buyer’s Journey – the buyer’s journey is a universal process that applies to any product or service. It typically involves stages of awareness, consideration, decision, and success. Understanding the buyer’s journey allows the salesperson to comprehend where the prospect is in their decision-making process and ask the most appropriate questions.
• Sales Process – the sales process, on the other hand, provides clear steps for the seller. It guides them on when to move to the next step, such as when to provide pricing to the prospect.
• Qualification process – this is a process used to evaluate and score deals based on their likelihood of becoming customers. It helps a company focus its sales efforts on the most promising opportunities, saving time and resources. Additionally, a qualification process allows a company to forecast its sales and revenue more accurately. 

How do you align your sales processes and CRM for a prospect-centric approach?

A typical sales process has four to seven stages – this is a rough number, but having too many stages can make the process ineffective. A company usually has a sales process that resembles an internal workflow instead of one based on what the prospect needs to do. “Prepare Pricing” vs. “Proposal Review” is a simple example of stages focused on internal workflow compared to what a prospect will go through. Get your sales team to think more about the prospect’s process instead of the internal one. 

Integrate the qualification process into the CRM – make room in the CRM for qualification-based results. Ideally, a manager should be able to use the CRM to score each opportunity and assess the quality of each based on the steps in the qualification process.

Stage gates and triggers shouldn’t be based on the seller’s whim – although you may have experienced salespeople, you don’t want to leave it to their judgment as to when a prospect should get pricing, for example. To trust your sales KPIs, you need consistency around why a prospect is in a certain stage. Therefore, each stage should have a trigger based on a prospect’s identifiable outcome, or something the prospect must do that indicates it’s time to go to the next stage. 

How do you need to think about qualification criteria?

Qualification criteria offer a structure for Sales to determine what they need to know about a prospect – this framework guides the sales team, helping them understand what questions to ask and providing a roadmap of communication with the prospect. It also shortens sales cycles by clearly identifying what’s required for the prospect to get to a decision.  

Qualification criteria provide the ability to forecast accurately – most Founders and CEOs have been in frustrating conversations with the sales team about the potential closure of opportunities. In some cases, it leads to a filibuster from the salesperson as they dance around the fact that they have no idea when or if it will get to a contract signed. Implementing a qualification process can alleviate this issue by ensuring everyone on the team understands what constitutes a promising opportunity. This leads to more effective sales meetings and accurate forecasting.

There are several off-the-shelf qualification structures, but they’re better as a starting point – structures like BANT or MEDDICC can be used, but it’s often beneficial to create a qualification process that’s specific to your product or service. This ensures the sales team knows what the company deems relevant for a prospect. If using a standardized version, MEDDICC, for example, is a good framework for more sophisticated buying processes, while BANT may be better suited for a transactional sale.

The goal is to streamline the process and get more ‘no’s’ from your ‘maybes’ – the goal is to improve the function of qualifying potential customers by increasing the number of clear rejections from those who are currently uncertain. This is important because salespeople typically have a limited number of “Closed Won,” a slightly larger number of “Closed Lost,” and a significant number of uncertain prospects. The ultimate objective is to help identify promising opportunities and streamline sales. By quickly identifying unlikely prospects, the team can focus on more promising leads, saving time and investing resources in those with a higher likelihood of success.

How should you build out your sales tool stack as you scale? What types of tools should you use?

Sales tools can aid in managing and tracking leads – tools to consider include:

• CRM –  a Customer Relationship Management tool- must-have for any sales team.
• Scheduling Tools – these are essential for managing appointments and meetings efficiently.
• Sales Intelligence Tools – tools like ZoomInfo, Seamless, Apollo, and LinkedIn Navigator provide valuable insights and data for sales teams.
• Proposal and Quote Management Tools – as the company grows and becomes more sophisticated, these tools become necessary.
• Sales Enablement Tools – tools like Gong or Wingman can be implemented once the team grows to about three people. These tools help in training and enabling the sales team to perform better.
• Digital Sales Rooms: for more sophisticated sales cycles, tools like SalesReach are secure online spaces where sales reps and buyers can work together and access relevant content throughout the deal cycle. It’s an easy-to-create customer-facing portal that simplifies the sales process by providing easy access to content, stakeholders, and communications and tracking customer engagement and feedback.

Sales Organization

What does your sales org chart look like at 2, 5, and 10 employees? What titles and skill sets should you hire for as you scale?

What can you do to ensure you find and hire great salespeople? What should you look for? 

Start any hiring process with a clear understanding of what you want and need – when hiring a salesperson, be clear on what attributes and skills you need. Consider what parts of the sales cycle the person will need to excel at over others. It could be creating new opportunities, identifying solutions within a prospect’s environment, or doing virtual meetings effectively.   

Once you’ve created a list, have all interviewers hiring for the same things – after creating a list of desired qualifications, it is recommended to create an interview guide for those conducting the interviews. The guide should include a rating system, such as a scale of 1-5, or poor to excellent, for each trait and space for note-taking. Each interviewer should prepare their own questions based on the desired qualifications.

Hire a mix of industry and sales skillsets early on – as mentioned, when hiring your first two account executives, consider hiring a combination of individual skill sets. For example, one person might have a lot of sales experience but no industry experience, while the other might have a lot of industry experience. This mix can help your organization grow and learn.

Consider using recruiting firms that specialize in hiring salespeople for niche hires – if you require expertise in a particular industry, certain recruitment organizations can assist you in finding individuals with these skills and start justifying recruitment fees. Additionally, irrespective of the necessary skills, a recruiter can discover passive candidates (those not actively seeking employment) who usually make excellent candidates.

Ensure that if you promote from within, the salesperson has coaching experience – when selecting the first manager, many organizations turn to their top salesperson. However, this approach may not always be effective. The crucial skill required for the first leader is the ability to coach, which is distinct from the ability to sell. It is more important to identify someone who can elevate the entire team than to feel obligated to give the best salesperson a shot.

How should you design your onboarding process for new sellers to maximize their chances of success?

Document the process and set expectations – the onboarding process should be well-documented and should clearly set expectations for the new employee. They should know what’s expected of them in the first month, quarter, and year. A system of regular feedback and performance evaluations should also be in place to ensure continual growth and improvement. Additionally, integrating new hires into the company culture from the get-go is essential. This fosters a sense of belonging and can positively impact job satisfaction and performance in the long run.

Onboarding is eased by having quality sales infrastructure – the success of your onboarding process often relies on the quality of your sales infrastructure. Implementing established processes like qualification and messaging can simplify and expedite the onboarding process and give new sellers a framework to follow.

What training, coaching, and sales enablement resources should you invest in for your sales org as it scales? 

Build out case studies – having case studies are necessary for the sales team. Case studies can establish credibility and trust with potential clients, showcase the unique value and benefits of your products or services, and provide a deeper understanding of how your company operates and solves the same problems they are facing. 

Create a First Meeting framework – establishing a format for the initial meeting is even more important than collateral. This format should detail the structure of the first meeting and the data that should be collected and learned about potential customers. This will assist salespeople in determining the next course of action and whether a subsequent meeting is required. 

Write out Demo Scripts – creating a product demo script can be a valuable tool to assist salespeople in presenting the product in a way that meets the needs of potential buyers and boosts their confidence and credibility. Such a script can guide the seller through the demo and ensure that the product is presented effectively.

Provide Sales Enablement / Coaching tools for virtual calls – using tools such as Gong, Wingman, and Read.ai can be highly advantageous for both sales leaders and sellers. These platforms offer coaching opportunities and ensure sellers remain on track, avoid dominating conversations, and effectively handle objections. With their increasing popularity, these tools have become valuable assets enabling sales teams to succeed.

How do you ensure effective communication and collaboration among your sales reps as the team grows in size?

Hold regular coaching meetings – regular one-on-one and coaching meetings are essential for effective communication and collaboration. It is important to distinguish between micro-managing and coaching during these meetings. Sales representatives do not appreciate micro-managing, but they do value effective coaching.

Your focus should be to help that seller be the best seller possible – as a leader, your main goal should be to assist your sales representatives in becoming the best possible sellers they can be, even if this means they may eventually outgrow their current roles. In discussions with them, it’s important to concentrate on the results they achieve rather than the activities they engage in. There should be less need to delve into specific activities if the results are satisfactory.

Analysis

What KPIs should sales function, teams, and individual sellers track? How do they change as you mature? 

In the early stages of scaling up sales, resist the urge to track too many KPIs – instead, focus on two quick-win metrics that directly fuel growth:

• Opportunities created per rep: This tracks new sales pipeline generation. Aim for each rep to create 5+ new qualified opportunities per month.
• Sales cycle conversion rate: This reveals how efficiently you convert opportunities to closed deals. Look to improve this by 10-20% quarter over quarter.

Keeping the sales KPIs simple lets you gain visibility into the specific activities driving revenue. As you scale, you can layer on more advanced metrics around deal velocity, win rate optimization, and sales productivity.   The key is tying sales data back to the big-picture business growth you want to achieve in the next 1-2 years. With clear visibility into pipeline generation and conversion, you gain insight into fine-tuning your sales engine to meet aggressive revenue goals that propel the broader success and valuation of your SMB.

KPIs should look at leading indicators, not just lagging indicators – leading indicators can help predict outcomes and provide insights into future performance while lagging indicators only reflect past performance. It’s important to base your KPIs on who you deal with, whether the board or other stakeholders. Your KPIs should be clear, easy to understand, and focus on the same objectives.

KPIs can be tailored to individual account executives – different AEs may have different strengths, with some excelling in attracting new prospects while others are better at converting existing ones. By tailoring KPIs to each AE, their performance can be optimized.

How should you think about setting quotas, compensation, and incentives? 

Start with conservative targets – when establishing sales quotas and targets, it’s wise to start on the conservative side. As a CEO, you may not have full visibility yet into the sales team’s capabilities or the nuances of your market. Beginning with modest goals reduces the risk of demoralizing your reps with unrealistic expectations. As you gather data and insights, you can course-correct and raise targets accordingly.  

Incentivize the right behavior – it may sound simple, but it’s often overlooked. The incentive plan must align with your broader business goals when structuring sales compensation. Take time to identify the specific behaviors and outcomes that fuel growth for your company. Do you want reps to focus on landing new logos? Growing existing accounts? Both? With strategic objectives defined, build commissions and bonuses to reward those desired behaviors.  

Be mindful of upselling compensation – when structuring sales compensation for upsells and cross-sells, be careful not to over-incentivize existing customer monetization at the expense of new logo acquisition. Offering the same commission rates for upsells versus net-new customers can inadvertently signal that renewals and add-ons are the sales team’s first priority.

Set quotas based on gross margins – quotas are often set arbitrarily, usually at four to five times the on-target earnings (OTE). When establishing sales quotas, resist the temptation to simply multiply target earnings by an arbitrary factor. Instead, consider your profit margins carefully to set quotas grounded in your financial realities. For example, a $250K OTE and $1M quota may be reasonable for a business with 60-70% gross margins. But with lower margins of 20-30%, attaining $1M in revenue would not yield nearly enough profit to sustain those commissions.

Use special incentives for low margins – for businesses operating on thin gross margins, creatively supplement base compensation to maintain attractive on-target earnings. Introduce performance accelerators and bonuses to increase overall OTE. For example, offer quarterly bonuses for reps who exceed sales or productivity quotas. Or consider a revenue consistency bonus for reps who consistently hit targets each quarter, incentivizing stable performance.

When structuring compensation for BDRs, avoid over-focusing on activity metrics – basing pay solely on the number of calls made or emails sent can drive mindless activity without results. Instead, consider incentives based on outcomes and impact. For example, comp BDRs on completed meetings rather than just scheduled calls. Additionally, factor in quality by integrating a no-show rate into earnings. This discourages setting sketchy meetings that customers don’t attend. 

How can you set your sales team up for accurate forecasting?

Have a well-defined qualification process – accurate forecasting depends on a well-defined qualification process that goes beyond simply asking AEs about deal status. This process should include clear criteria and be placed above your sales process. It may require identifying an economic buyer, establishing a timeline, gathering budget details, and securing a champion. Standardizing qualification ensures consistency, giving you a trustworthy forecast that accurately reflects the health of each deal.

Prioritize opportunities with a high likelihood of closing – when building sales forecasts, resist placing undue weight on the largest potential deals in your pipeline. While big-ticket opportunities may seem attractive for projections, they often come with higher uncertainty. Instead, prioritize opportunities with the highest likelihood of closing when compiling your forecasts. Again, a clear qualification process will determine which deals can close and close in the current month. 

AEs need to be prepared for forecasting meetings – for efficient and accurate forecasting meetings, equip your account executives to answer key questions confidently. With a strong qualification process, you should be able to score each opportunity based on the answers you hear from the AE. When the process is understood, they already have a command of each deal’s status by asking prospects the same details you’ll inquire about.

Overall

What are the most important things to get right?

Establish a strong sales infrastructure – this answers the question, “How do I scale from 1-10+ sellers”. When you rapidly expand your sales team, a lack of consistency can become your biggest obstacle. But a strong infrastructure provides standardization and continuity even amid growth. It’s the key driver that takes your team from operating consistently to delivering consistent revenue growth.

Get the right people in the right seats – hiring for sales roles goes beyond evaluating skills and experience – assess cultural add and alignment with the company’s vision. Seek talent motivated to execute on your specific goals and sales methodology. When assigning responsibilities, match team members’ capabilities to roles that play to their strengths. With nuanced talent/role fit, your sales team can perform cohesively at its full potential.

Incentivize the right behaviors – for sellers handling multiple responsibilities, you’ll want to craft targeted incentives to promote desired behaviors beyond their core role. For instance, consider higher commission rates on self-sourced deals. This motivates them to carve out time for proactive outbound prospecting amidst their wide scope, bringing in new accounts to supplement the existing book of business. Overall, let intended behaviors guide compensation design. Identify gaps in current activities, then engineer plans to steer reps toward those high-value efforts. Targeted incentives enhance multifaceted roles by prioritizing key growth-driving activities amongst a sea of responsibilities.

Provide strong leadership – a thriving sales culture stems from strong leadership. A leader should demonstrate the ability to strategize, motivate, and develop talent. Your sales leaders should mentor reps on honing their craft while inspiring peak performance. Foster collaboration and accountability balanced with empathy and support. Maintain visibility into team challenges without micromanaging operations. Although coaching and culture building are the most vital attributes of a sales leader, experience in constructing a strong sales infrastructure is also crucial. This need for varied expertise makes hiring a full-time sales leader costly and is why fractional leaders are an option worth considering.

What are common pitfalls?

Acceptance of inconsistency – one of the major pitfalls when scaling from one to 10+ sellers is the acceptance of inconsistency. Without vigilance, disparities can creep in regarding marketing alignment, messaging, sales processes, prospect follow-up, and opportunity qualification. Left unchecked, this variability in approach undermines growth. It leads to disjointed, confusing customer experiences that fail to convey your value. The solution lies in establishing a strong underlying sales infrastructure before scaling up. 

Failing to build a sales culture – a robust sales infrastructure enables consistency and forms the bedrock for building a thriving sales culture. With standardized systems in place, your team feels empowered to execute consistently at a high level. Over time, this solid infrastructure fosters confidence, motivation, and camaraderie. Sales professionals feel immersed in a culture that sets them up for success through clarity of expectations and coordination. So while infrastructure builds consistency, it also allows a winning culture to blossom organically from a place of reliability, stability, and support.

Disrupting the role of the Founder without a plan – when a founder aims to step back from leading sales, carefully plan the transition to maintain continuity. Sudden leadership voids without succession strategies disrupt operations and progress. Resist immediately handing off sales oversight to an unprepared successor or imposing a new external leader lacking company and culture context. Instead, consider leveraging an experienced fractional sales leader as an interim step. They provide structured leadership and strategy to guide sales, letting the Founder focus on broader company-building