Move from founder-led sales to scaling a sales team

My team works with many SaaS startups, and about 40% of their sales motions are driven by founding teams, while others that are scaling fast are learning to transition from founder-led sales (FLS) to sales-team-led sales (SLS).

To grow your company, you need to create sustainable sales operations. To this point, you’ve been grinding late nights for at least the first three years, and there’s a lot of core knowledge you’ve built up that needs to be transferred into other people’s brains — and a documented sales process.

The hard truth is that you’ll never be able to walk away from a direct sales involvement role. You can, however, staff repeatable sales functions (prospecting, demos, negotiation, contracting, forecasting) to give you more time to focus on strategic partnership development and public relations cheerleading.

My posts aren’t short, so do your best to stay focused throughout the read, as you and I will cover everything you need to improve the founder-led sales flow through to scaling your startup sales team. I also ran this post by seven well-funded SaaS founders to pack in as much knowledge as possible.

At what point should startups transition from a founder-centric sales approach?

Consider moving away from a founder-led sales process when scaling and complexity of operations demand a more structured and specialized sales approach. Here are the key indicators of when to hire your first salesperson:

• When the volume of sales inquiries and customer interactions exceeds the founder’s capacity to manage effectively. For instance, if a startup specializing in e-commerce software begins to receive a high volume of inquiries from different global markets, the founders may struggle to handle these alongside their other responsibilities. This situation requires a dedicated sales team to manage these relationships and ensure each client receives the attention they deserve.
• Need for specialized sales expertise. As a startup grows, the complexity of sales negotiations and the diversity of customer needs often require skills that go beyond the founder’s expertise. For example, negotiating large contracts with multinational corporations may require sales personnel with specific industry experience and negotiation skills.
• Need for focused product development or strategic leadership. Founders must allocate more time to guide the overall direction of the startup, leaving sales to experienced professionals who can optimize and expand the sales process efficiently.

After you establish it’s time to start scaling your sales operations, follow these steps:

1. Hire your first SaaS sales role

There are a lot of role-based acronyms in the sales world that can cause hyperventilation, so I’ll make it easy for you to understand which skills from all of these roles you actually need for the first sales hire. Remember that the first sales hire will be a multi-role person borrowing key aspects of what is typically done by multiple people in larger organizations.

Frankly, you just need a killer who wants to do a tad of everything, someone who doesn’t whine about staying late, can handle a shit load of stress and is able to work with a blank slate to create new processes.

If you do the handoff right, they should be overwhelmed working with you for the first half year (and you should manage their expectations in the hiring process). But you’ll reward them handsomely as this sales unicorn is the person who — ideally — will build your future sales team.

Here’s what to look for in your first sales hires

Use this as a quick checklist to hire your new salespeople:

1. Borderline offensive humor
2. Knows how to shoot the shit with prospects about anything
3. Has an “I’ll figure it out attitude” — meaning: doesn’t need diaper training
4. Has drive, comes up with new processes, sources own tools and gets the job done however it needs to be done
5. Ideally, has experience in the target company type you are trying to sell to or a proven track record in a similar business as yours
6. Knows how to navigate sales software like Apollo, Lusha, Sales Navigator, SalesLoft etc
7. Asks questions about every facet of the product and service
8. Shows evidence of meeting or exceeding sales targets in previous roles
9. Is able to balance between aggressive startup sales strategies and maintaining integrity
10. Contributes positively to the team dynamic
11. Shows a commitment to continuous learning and self-improvement

Know the key attributes of sales roles

Let’s review five typical sales roles in organizations with over 100 people and what attributes you need to take from each role to craft your startup sales team.

Business development representative (BDR)

The person who actually pulls in the leads before handing them off to the SDR to close the deal. I love the tenacity of a great BDR, from pounding the phones, emails and social messaging — this person is a stalker you need. And with the advances in sales AI technology, one person can literally do the job of five people as long as they know how to leverage AI tech within their daily workflow. In large organizations, their traditional role is to pound the phone and send scripted email sequences. Think of BDRs as your front-line soldiers who actually know the smell of napalm in the morning.

• Daily job: Calling and following up with an assigned or harvested list of prospects.

• The insight they have: 

• • Customer objections and how to handle them.

• • Customer reasons for looking for a new alternative to the solution they currently use.

• • Being able to right-size a calling list, specifically, whom not to contact.

• What you need: Everything from this role plus two years of experience in a SaaS sales role.

If you want to enable your BDRs, ensure they have ready access to the following information (bookmark these links and read them later):

• 📙 Ideal customer persona document
• 📙 Competitor matrix document
• 📙 Messaging framework document

Note that, if you are a fresh startup, you probably won’t have this collateral ready for them or it will be super high level. It is expected that your first sales hires can piece this information together within the first three months of working with you.

Sales development representative (SDR)

SDRs typically work on inbound leads generated from BDRs, effective SEO and content programs. They run the initial couple of demos before closing a deal or getting help from sales engineering/product to close the deal. SDRs are more useful for fast-scaling organizations that require layers in the sales team due to the overflow of leads coming in both from outreach and inbound efforts. This role is usually more senior than a BDR, as they are required to bring the deal to a close.

• Daily job: Qualification meetings, client research and demo prep, demo walk-throughs, contract negotiation.
• The insight they have: Feature requests, common pain points, ideal customer-to-product fit and common contract negotiation push-back areas.

What you need: You don’t need this role as your first hire since you are already in that role. However, once you’ve settled with your first sales hire, this professional will move into the SDR and lead role while you both hire new BDRs based on the sales motion you’ve now been able to create.

Account executive (AE)

They work on existing accounts to ensure killer service delivery to keep the net promoter score (NPS) high. Their actual goal? Retain the client and upsell the living shit out of them (with new features, add-ons, perks etc). The AE must be focused on relentless customer success, keeping a pulse on all customer likes, dislikes and ideas.

• Daily job: Intake new feature requests, deal with feature and service complaints, support onboarding, update the customer on new features/modules and build brand advocates.
• The insight they have: 

• • Customer frustrations with features and services.

• • Customer “aha” moments with features and services.

What you need: If your solution is high-touch from an account management perspective, you’ll need this role after your first 15 to 20 clients. Until then, your project managers (PMs) and SDRs should be maintaining the sold-to accounts.

Partner development representative (PDR)

A role that shockingly has the least amount of online articles and video coverage is the role that is the secret sauce to influential, long-term relationships that can triple your sales referrals. PDRs build strategic high-value relationships with established vendors playing in your space to help with routing leads your way. Unfortunately, great partner relations professionals are insanely hard to find, are settled in great roles and require an extreme amount of funds to poach away from their current role.

Aside from hiring, the best way to build this role is to train/promote from within your company (this is the AEs next growth step).

• Daily job: Build and maintain strategic relationships via partner programs.
• The insight they have: Market feature demand, market pricing, detailed competition landscape and partner-end influential role mapping.

• What you need: There’s a massive shift to partner-led sales within B2B SaaS, so you might actually need this role as of year two of your startup. I suggest tuning up the sales processes prior to hiring this role so that they can actually focus on relationship building vs turning into a hybrid AM.

Summarizing the essence of the roles above, it’s easy to understand which people you should be eyeing to onboard first. Now, if you have ample new funding, this doesn’t mean you need to hire all of them. That’s going to be a disaster, as a new team without experienced guidance is ineffective.

What you should do instead is hire the core roles under a solid sales leader, then hire based on what the sales leader tells you.
Use this sales team responsibility table to help you put things into perspective:

Attributes	Business development	Sales development	Account Executive	Partner development
Objection handling	X
Relevant prospect targeting	X			X
Reasons to switch	X	X
Best to be a future sales leader	X	X	X
Pain points	X	X	X
Competitive landscape		X	X	X
Customer “aha” moments	X	X	X
Customer frustrations		X	X
Bridge between sales and product team			X
Maintain client NPS			X	X
Build strategic partners as sales channel				X

A sample sales role job responsibilities

• Uncover and qualify prospective customer needs, understand business processes, identify opportunities, understand requirements and ascertain potential areas to add value.
• Research target companies and key decision makers to identify their business challenges and need for our solutions.
• Effectively introduce and represent the product.
• Write compelling emails and tell engaging stories that leave prospective customers wanting to learn more about the value our product delivers.
• Schedule opportunities to engage with prospects and members of the sales team.
• Collaborate with sales and marketing to continuously improve our lead generation and follow-up process.
• Ability and capacity to qualify the account for short- and medium-term opportunities.
• Accurately update CRM software with customer data.

Save this link for later 👉Your sales team should have a value-creation mindset.

2. Build a no-nonsense sales compensation plan

To keep your startup sales team motivated, build a no-nonsense sales compensation plan that is easy to pay out (not a nightmare for accounting) and easy to track for salespeople so that their morale is high.

Here’s my recommendation on sales compensation plans to start with:

• % from deal total: An easy plan where you pay a percentage from the total deal on invoicing (after taxes, of course). Just ensure that periods are established that are convenient for accounting to pay out monthly, quarterly, or yearly.
• % from upsells: Also an easy comp plan that pays for upsells on existing clients. Ensure that this percentage is smaller than a new deal since working with an existing client is much easier than attaining a new one (where all your efforts should be going in the first couple of years).
• % from partner referrals: This comp plan rewards building relationships with partners and influencers. The compensation amount should be the same as a new deal as it’s hard to build long-lasting strategic partnerships that enable your sales process.
• % for exceeding the target within xx months: Also relatively simple to do, this compensation ramp-up helps you motivate salespeople to overachieve their basic targets and close more logos.
• $ for # of relevant demos booked: This incentive is based on pure reach-out activity, primarily used for BDRs and some SDRs. The danger with this comp plan is validating the quality of the leads booked for the demo. This means having your ICP hammered out in detail prior to enabling this plan. Only compensate for qualified demos booked.

Software advice: I’ve been in sales for over 12 years, and the only sales compensation software actually worth your time is QuotaPath. However, if you’re a team of under five, figure it out in Google Sheets first. Yes, you’ll need to know how to do the grade 3 maths.

Here’s a fantastic post by QuotaPath on building compensation plans for startups. I’d recommend starting with a simple single-rate commission plan + accelerators for over-achievers.

⚠️ Note that salespeople typically sue organizations due to unclear/lack of transparency in sales commission payouts, as they believe they are not being compensated fairly per their contract. So, keep things simple to prevent low performers from taking advantage of your company.

3. Set up the sales process

Did you make it this far down the post? That’s why you’re a go-getter. Let’s keep rolling, as getting this part right is what will scale your startup and get the board and investors off of your back — for a short while at least. So how do you set up the sales process?

3.1 Start with basic sales and forecasting metrics 

At the start, you obviously won’t have any sales KPIs pumping in your CRM, and your dashboards will look blank. That’s cool, as you start your reach-out activity, you must ensure you have the following views easily accessible (you can build the below sales metrics reports in any CRM):

• Prospects touched: This metric refers to the total number of potential customers or clients that have been contacted or reached out to. It’s a measure of outreach activity.
  • Example: If your sales team sends emails to 100 different prospects, your “Prospects Touched” metric would be 100.
• Conversations had: This metric tracks the number of meaningful interactions or dialogues that have occurred between a salesperson and a prospect.
  • Example: Out of 100 prospects touched, if sales reps have in-depth discussions with 25 of them, your “Conversations Had” metric would be 25.
• Demos booked: This metric counts the number of demonstrations or presentations of your product or service that have been scheduled with prospects.
  • Example: If 10 out of 25 prospects with whom conversations were had, agree to a product demo, the “Demos Booked” metric would be 10. Your demo booking rate is 40% (10/25).
• Lead response times: This metric measures the average time taken by sales team members to respond to a new lead or inquiry.
  • Example: If new leads are responded to within an average of two hours, your “Lead Response Time” would be two hours.
• Lead to win rate: This metric calculates the percentage of leads that eventually convert into paying customers.
  • Example: If five out of 100 prospects touched become customers, the “Lead to Win Rate” is 5%.
• Sales cycle length: This metric tracks the average duration taken from the first contact with a prospect to closing the deal.
  • Example: If it typically takes 30 days from initial contact to deal closure, your “Sales Cycle Length” is 30 days.
• Average deal size: This metric averages the value of deals closed over a certain period.
  • Example: If five deals are closed worth $1,000, $2,000, $1,500, $3,000 and $2,500, respectively, the “Average Deal Size” is $2,000.
• Average Cost per Lead: This metric calculates the average expense incurred to acquire each lead.
  • Example: If you spend $1,000 on marketing and generate 50 leads, the “Average Cost per Lead” is $20.
• Customer acquisition cost (CAC): This metric measures the total cost associated with acquiring a new customer, including marketing and sales expenses.

Example: If your total sales and marketing expenses are $10,000 and you acquire 10 new customers, your CAC is $1,000 per customer.

3.2 Navigate the art of prospecting

By now, you should be a master of your ICP at the very least. So ensure you communicate to your new sales protege how you’ve been finding the right fit clients. I know it is not always this simple since you might have harvested clients from existing relationships; in this case, you need to identify why your current client portfolio is using your product/service and who else is just like them in industry, geography, company size, technology usage and so on.

To absolutely crush this process, I highly suggest you and your first sales hire to focus on the following items:

The first 20 deals must be closed by and with the founding team

Somewhere above, I mentioned knowing the smell of napalm in the morning… Well, this is it. As a founder, you must pair up with partners to close your first (at least) 20 deals to really understand what it takes to find, nurture and close a business.

This way, you’ll be able to train your future sales team on the typical questions, objections and other negotiation tactics that come with the territory of winning business in your industry. And what better way to train someone than going through the rough times yourself — lead by example, folks (and dive into it even as you scale later to monitor, coach and learn something new from the team).

You need over 1 million in annual recurring revenue, and it’s the hardest thing to do

One million sounds like a lot of money, because it is. It’s also the hardest thing to get to. Once you’ve made your first million, believe me, replicating that million into two is half as hard, and you’ll be setting your sights on the first 5 million and then 10 million in no time.

Why am I speaking about the first million? Since you don’t need a sales team to get to it — at all. It should be just you and, hopefully, your founding partner/s. Then, go out and look for a sales hire as, by this time, you’ll have a basic grasp on how and whom to sell to.

Now this is the ideal way of going about it, naturally if you are newly funded and there are ample funds available, then you should be involved on all sales calls until you hit that first million (so you understand what it takes to get there).

Don’t overshare

Want to earn someone’s trust? Talk less and listen more this goes both for you and the sales team. The worst thing to do in sales is to machine gun through a presentation without asking questions and pulse-checking the disposition of your prospect. Read the room, understand why they came to the call (their pressing problem) and how you can align a solution to sell to them. Oversharing useless information just leads to the prospecting feeling like they’re not listened to and opens massive gaps for you to make mistakes during the pitch.

The show is about them, not you.

Don’t give too many options to avoid choice overload

Guess what humans tend to do when presented with too many options? They tend not to choose since it is easier to fall back into their comfort zone versus doing extra homework on a new concept. You need to ensure that when prospects walk away from the presentation, they have a maximum of three messages to remember about your business and how easy it is to try your product. Here’s what that looks like for our business:

1. Our team specializes in B2B SaaS demand generation. That’s all we do.
2. Everyone is in-house. We do not use contractors as we’re quality obsessed.
3. We’re a proactive team trained to help your internal team do more.

🧠 Geek out by reading the psychology behind choice overload, as they do a way better job than my short paragraph above.

Make it easy to buy and terminate

It’s the worst thing when someone wants to buy from you but the process is convoluted like getting a tourist visa to North Korea 😂. Here’s what makes buying suck and quick fixes for it:

1. A lousy account creation experience: You’re not suicidal with the business, right? So ensure your sign-in and create-an-account pages are clear in their value proposition and the process to create the account and sign into an account is stupidly intuitive.
2. A dull/confusing onboarding experience: Now that you’ve sold to your customer (congrats!), you actually need a human (account manager) to reach out and walk them through the first steps, or make sure there is an on-screen demo that guides them through the basic setup.

Prospecting is never perfect. This sales process is also heavily influenced by environmental factors like technology shifts — e.g., the introduction of AI email blockers, spam filters, the shift to hybrid work impacting call outreach and so on.

Once you accept that the prospecting process group will need constant tuning, you’ll enjoy the challenge, and it’ll become part of regular sales ops.

Software advice: You’ll need a couple of tools: Hubspot CRM (to capture, track and nurture leads), Apollo (to get lists and automate reach out) and Lusha (to get call lists) are a good start.

📙 Save this link for later and thank me later: How to create a killer “get a demo” page

3.3 Prove your pitching game

This is the secret sauce of every company. Although I can’t possibly teach you how to pitch your business better, I will tell you the tactics that will make your pitching process much more effective.

Master the art of question-based sales (QBS)

Ditch the pitch and embrace the power of questions. Asking thoughtful, targeted questions isn’t just about gathering information. It’s about unlocking pain points, building trust and guiding prospects toward your solution.

Why are questions so potent?

• Unearth pain points: Prospects rarely volunteer their deepest struggles. Your questions become a scalpel, uncovering hidden inefficiencies, bottlenecks and frustrations they might not even fully recognize.
• Build rapport and expertise: Asking insightful questions demonstrates you understand their industry and challenges. This positions you as a trusted advisor, not just another salesperson.
• Tailor your solution: Generic presentations fall flat. By understanding their specific needs, you can tailor your offering to directly address their pain points, increasing relevance and value.
• Qualify leads faster: Asking the right questions early saves time and energy. If their challenges don’t align with your solution, you can gracefully move on instead of wasting time pitching a poor fit.
• Close deals smoothly: When prospects actively participate in the sales conversation through your questions, they feel more invested in the solution and its potential impact. This increases buy-in and facilitates smoother deal closure.

Example questions for SaaS sales:

• Marketing automation: “What marketing tasks are currently the most time-consuming for your team?”
• Project management: “Have you encountered any challenges in keeping your team aligned and projects on track?”
• Customer relationship management: “Do you struggle to gain a unified view of your customer interactions across different channels?”
• Accounting software: “Are there any manual processes in your accounting department that you’d like to automate?”
• HR software: “What are the biggest pain points you face in recruiting, onboarding and managing employee data?”

Remember, questions are the key that unlocks value. By mastering the art of inquiry, you’ll not only sell your SaaS solution but also build lasting relationships with your customers.

📙 Read on how to run a question-based sales process.

Know how to add just enough value with prework and have a consultative approach

Don’t dive headfirst into a sales call. Instead, demonstrate your value beforehand through targeted pre-work just set a target on how many hours is too many for working a prospect. For example, are 100 hours of research and pitch creation worth this opportunity? This sets the stage for a meaningful conversation, fostering trust and positioning you as a true partner, not just a salesperson.

Why is this crucial?

• Show genuine interest: Investing time in pre-work (industry research, competitor analysis, personalized reports) shows you care about their specific needs, not just making a sale.
• Set the agenda, not the pitch: By understanding their challenges through pre-work, you can tailor the call to address them directly, creating a more relevant and valuable experience.
• Become a trusted advisor: Sharing insights and recommendations based on your pre-work positions you as an expert, building trust and credibility long before the pitch.
• Qualify leads efficiently: Pre-work can reveal if their challenges align with your solution, saving time and effort by filtering out poor fits early on.
• Start the close early: By laying the groundwork with valuable insights, you’ve already begun addressing their needs, making the transition to discussing your solution a natural progression.

Remember, consultative selling isn’t a one-time event. It’s a mindset that influences every interaction. By prioritizing value over pitch, you’ll build trust, create engaged prospects and close deals with confidence.

Know the limits of building a POC

A lot of founder-led companies lose a lot of money on building a proof of concept (POC) for their prospect. Don’t be that guy and know the critical features within the POC that will show the customer enough value for them to make a decision with you. The best POCs are paid for (plus, you know for a fact that the prospect is serious about the purchase), so do your best to sell POCs and not give them out for free.

Learn to handle objections

Objections are not roadblocks, but opportunities to build trust and close deals. Prospects raising concerns reveal their genuine interest and allow you to address their specific needs. Effectively handling objections helps overcome initial hesitation but also showcases the true value your solution offers.

Sales objection	Way to handle/Respond
It’s too expensive	Acknowledge the concern about cost, then focus on the value and ROI the product delivers. Provide a cost-benefit analysis to demonstrate long-term savings or gains. Offer flexible pricing plans if possible. Reinforce flexible termination terms.
We’re happy with our current solution	Ask what specific aspects they like about their current solution to understand their needs. Highlight unique features or advantages your solution offers that their current one doesn’t. Offer a free trial or demo to showcase these benefits.
We don’t have the time to implement a new system	Explain the implementation process and provide an estimated timeline. Emphasize the support and training your company offers to ensure a smooth transition. Discuss the long-term time savings and efficiency gains post-implementation.
We need to think about it	Respect their need to consider and offer to provide additional information or references. Suggest setting a follow-up meeting to address any pending questions. This shows you're interested in their needs and decision process.
We’re not ready to make a change right now	Inquire about any specific concerns or timelines they have in mind. Offer to keep them informed with updates and industry insights, positioning yourself as a helpful resource rather than pushing for an immediate sale.
Your product lacks [specific feature]	If the feature is in development, provide a roadmap or timeline for its release. If not, discuss how your product’s existing features can meet their needs in different ways. Alternatively, talk about custom solutions if your company offers them.
We don’t have the budget for this	Discuss the product’s pricing tiers and check if a lower-tier plan might suit their budget. Highlight the potential ROI and how your product can help save or generate money in the long run. Explore alternative financial arrangements like payment plans if possible.
We need to consult with the team/decision-maker	Offer to provide additional materials or presentations tailored for their team or decision-maker. Suggest a joint meeting to directly address concerns and questions from the decision-making team. This shows respect for their internal processes.
How are you different from your competitors?	Clearly articulate your unique selling propositions (USPs) and how they benefit the customer. Use case studies or testimonials to demonstrate your product’s success and customer satisfaction. Be honest about what sets you apart without disparaging competitors.
We've never heard of your company	Introduce your company’s background, achievements and credibility in the industry. Share customer testimonials, case studies and press releases to build trust. Highlight partnerships or recognitions, if any, to establish your company’s reputation.

What are the essential elements of a compelling sales pitch for founders and early sales teams?

Here are elements to spice up your sales pitch and help you win that deal:

Storytelling:

• Share your “why”: Connect with prospects by sharing the story behind your company’s mission and how it solves a real problem.
• Highlight customer success: Showcase stories of existing customers who benefited from your solution, focusing on quantifiable results.
• Weave in your personal journey: Share your unique perspective and passion for the problem you’re solving to build trust and rapport.

Data and expertise:

• Emphasize your deep product understanding: Showcase your in-depth knowledge of your solution and its technical capabilities.
• Use data and metrics: Leverage case studies, white papers and statistics to back up your claims and demonstrate the value proposition.
• Tailor your pitch to the prospect’s needs: Understand their specific pain points and demonstrate how your solution directly addresses them.

Transparency and authenticity:

• Be upfront about challenges: Discuss the limitations of your solution and your plans to address them. Authenticity builds trust.
• Embrace the “startup hustle”: Share your journey and challenges, showcasing your resilience and commitment to building a successful company.
• Focus on building relationships: Prioritize understanding the prospect’s needs and concerns over a hard sell, fostering long-term partnerships.

A quick example: Zoom founders used their experience as engineers struggling with remote communication to create a compelling story that resonated with prospects, leading to their rapid growth.

3.4 Be diligent with the follow up

As simple as this sounds, it’s the most tedious and poorly executed part of the sales process since you’re not following up quickly enough — or you lack relevancy in your follow-up messaging. But overlooking a simple touchpoint is like leaving money on the table, especially in the cutthroat world of SaaS sales. Every minute you delay could be another rep closing the deal your prospect was on the fence about. Sure, following up feels tedious, but remember:

• It’s not about bombarding your prospect; it’s about nurturing a relationship. Personalized, relevant messages addressing their specific needs and concerns show you’re invested in understanding their challenges. This builds trust and positions you as a knowledgeable advisor, not just another faceless salesperson.
• While you’re silent, your competitors are actively engaging with that prospect. Don’t let them steal the deal simply because you hit snooze on the follow-up email.
• Use technology! Sales automation tools can help you stay organized, send timely reminders and personalize messages at scale. Invest in efficient systems that free up your time for crucial high-touch interactions.
• Timely follow-up isn’t just about closing deals, it’s about respecting your prospect’s time and building genuine connections.

By prioritizing prompt, relevant follow-up, you’ll not only land more deals but also cultivate loyal customers who advocate for your brand. Now, go forth and conquer that inbox!

3.5 Close the deal

The longer a B2B SaaS deal takes to close, the higher the chance of you losing the deal. So move fast, the typical non-pricing related losses are: 

• Your main point of contact has changed, so you’re now faced with starting from scratch and convincing a brand new person.
• Someone on the buying committee who is an influencer has changed, and now the buying committee needs to be reconvinced.
• A key contact has NOT been recognized early on in the deal and threw a wrench in your wheels.
• You got blocked by a technical role due to misunderstanding the technical requirements of the client and aligned the wrong solution.
• Some sort of compliance failure that wasn’t identified ahead of time.

To effectively close the deal, you need to map and understand your typical buyers’ journey. Without this, you’ll be leaving your lunch for someone else to eat.

👉 Learn what’s involved in a B2B buyer journey.

4. Get a lawyer experienced in your industry

With sales, come contracts and contracts have lots of T&Cs that you will WISH you have had a lawyer go through first. So to try and prevent that first lawsuit, your first couple of contracts (if they are unique, which they most likely will be based on customer asks) should be run by a legal professional that knows how to cover your team’s ass.

If you’re in SaaS, always pay special attention to the following sections:

• Processing of customer data (based on region)
• Storage of customer data
• Deletion of customer data
• Who owns the tech (the answer is you) when building a POC
• Security compliance (and proof of)
• Recurring fees and signup duration
• Termination clauses
• Uptime guarantees
• Support terms

There’s much more to it, but the above list is the birthplace of a world of hurt if it’s not worded right. When doing legal work, ask legal to keep it as plain language as possible. Yes, your contracts can avoid a lot of legal jargon.

5. Build a 360* go to market (GTM) practice

Why are we talking about GTM? Without actual marketing support, your sales efforts will be very expensive and less effective as they will not have supporting collateral that is often generated by the marketing and product teams. The good news is that you can get started on the collateral building prior to and in tandem with training your sales team. What you need:

5.1 Messaging

Before hiring a sales team, you must have your company’s identity aligned. This means understanding your company’s point of view and messaging. Having those two in place will immensely help a new sales team understand how to build out their call scripts and the types of messaging to test for prospect resonance.

• Problem statement: The specific challenge or need your product addresses, explained in terms that resonate with your target audience. For example, if you’re selling a time management app, the problem statement could be, “Helping busy professionals reclaim their time from chaotic schedules.”
• Positioning statement: Your unique approach to solving this problem and how it stands out in the market. Make sure to highlight your unique selling proposition and how it addresses key pain points. For instance, “Our time management app utilizes AI to automatically prioritize tasks, offering a unique solution to time-poor professionals unlike any other app on the market.”
• Core message: The central idea or theme that you want your brand to be associated with. This message should encapsulate your positioning statement in a memorable way. An example could be, “Empowering professionals to master their time with smart, AI-driven scheduling.”
• Benefit pillars: Concise summaries of the main advantages and features your product offers to customers. For a time management app, these could include “Intuitive Interface: Easy-to-use design that simplifies scheduling” and “Smart Notifications: AI-powered alerts to keep you on track with your tasks.”
• Proof points: Tangible examples or data that substantiate your benefit pillars. This could involve customer testimonials, statistics or case studies. For example, “User testimonial: 90% of our customers report a 50% reduction in time spent organizing their schedule” or “Case Study: How Company X increased productivity by 40% using our app.”

If you haven’t done a formal messaging exercise, I would jot down this task as homework now and finish it with your co-founders within the next two weeks. To help with this, read this post on startup brand positioning by Insight Partners.

5.2 Website, SEO, content

Once you’ve sorted your messaging, the next step is to ensure your website and content are congruent with your positioning and are optimized for enterprise SEO — meaning: the site must be working to capture inbound traffic, which will directly benefit your sales team.

📙 Get the primer on how an SEO project improves your demand generation efforts and cohesion across multiple departments.

Building your brand perception as an industry thought leader helps to win deals, too. In fact, a 2024 LinkedIn-Edelman study shows that nine out of 10 C-suite executives and decision-makers are more receptive to marketing or sales outreach from organizations that output high-quality thought leadership on a regular basis.

📙 Get to know our proven B2B SaaS content writing process.

5.3 Paid advertising 

Paid ads help you test ideas for resonance fast. Now, your sales cycle might be long, which will make attributing paid advertising against the influence of sales harder. Nonetheless, testing the resonance of your ads and keywords within ad groups will help supplement the SEO efforts.

5.4 Social

Just like paid advertising, social advertising and active posting on relevant channels will help attract the right people to your website. Most B2B SaaS companies use LinkedIn Ads via ebook download, webinar or a compelling demo offer. Just don’t forget that most people also spend their time on YouTube, Instagram and specific industry publisher sites.

Let my team enable your sales efforts

Between sales pitches, senior leadership team (SLT) meetings and the usual firefighting in startup life, I made time to write this blog for our website because there’s no better way to connect with prospects than showing that you get their pain points. You’ve been there.

By investing in your website (whether it’s outputting new solution pages, blog posts, case studies, white papers, webinars etc), you enable your sales team with marketing resources to educate prospects, showcase the value of your offerings, overcome objections and ultimately close deals more effectively.

And it’s where my team can help: from rebuilding your B2B SaaS website to running ads or writing SEO-ready thought-leading content.

Start by reviewing all our resources focused on startup funding and growth, then reach out to explore our digital marketing services.

Frequently asked questions 

Does the close ratio decrease as the sales team grows? 

There’s a common and often true claim that goes something like: “Always remember that the more you scale your sales operations, the lower your close ratio becomes (because no one will be able to sell better than the core sales team).”

The counterpoint: This statement overlooks several factors:

• Standardization and training: As you scale, you can implement processes and training programs to ensure all reps have the knowledge and skills needed to perform as well as the core team. This includes product expertise, sales methodologies and effective communication strategies.
• Specialization: A larger team allows for specialization, where reps focus on specific segments, industries or product lines. This can lead to deeper product understanding and more targeted pitches, potentially increasing their individual closing rates.
• Technology and automation: Sales tools like CRM systems, lead scoring and automated workflows can streamline processes, free up reps’ time for building relationships and closing deals and even provide data-driven insights to improve their pitches.
• Onboarding and coaching: Investing in a robust onboarding process and ongoing coaching can ensure new reps quickly reach their full potential and maintain high closing rates.

However, there are potential challenges to address:

• Maintaining culture and values: As the team grows, it’s crucial to maintain the culture and values that fostered success in the early days. This includes transparency, collaboration and a focus on customer success.
• Motivation and engagement: Keeping a large team motivated and engaged can be challenging. Implementing recognition programs, celebrating achievements and fostering a sense of community can help.
• Data and analytics: Monitoring individual and team performance closely becomes more important with a larger team. Utilize data and analytics to identify areas for improvement and provide targeted coaching.

Remember, success isn’t just about maintaining the same ratio as your core team; it’s about achieving your overall sales goals while building a sustainable and scalable sales organization. Will you take a hit at the beginning of building a sales team? Probably, but standardization, coaching and analytics will help you pull out of the slump and exponentially increase your sales reach.

What impact can founder-driven sales have on the evolution of product development?

When startup founders engage directly in sales, they tend to acquire immediate and authentic feedback from clients, offering invaluable insights into the users’ needs and preferences.

Consider, for instance, a scenario where a founder demonstrates their LMS to a potential client. During the interaction, the client expresses a need for advanced analytics features to track employee training progress more effectively within one dashboard view. This direct feedback is a goldmine for the founder, who can quickly relay this information back to the development team. As a result, the LMS can be updated to include more sophisticated analytics features, directly addressing the needs identified during the sales process.

Such hands-on involvement ensures that the product evolves in line with real-world user requirements, keeping the product relevant and competitive. It also helps identify market trends and customer pain points, enabling the startup to stay ahead of the curve. This approach not only improves the product but also strengthens customer relationships, as clients see their feedback being taken seriously.

📙 Save this link for later: How product-led growth helps startups scale

How do I balance sales responsibilities with other founder duties?

It’s a juggling act! Here are strategies for founder-led SaaS sales amid a sea of responsibilities:

Prioritization:

• Identify mission-critical tasks: Analyze which founder duties directly impact sales and prioritize accordingly. For example, product development might be crucial, while legal work could wait.
• Timeboxing: Allocate specific times for sales activities (pitching, demos, follow-ups) and stick to them. Consider the Eisenhower Matrix to categorize tasks by urgency and importance.
• Leverage tools: Use project management platforms and automation tools to streamline non-essential tasks and free up time.

Delegation and outsourcing:

• Can a co-founder or freelancer handle tasks? Delegate marketing, customer service or administrative duties to free up your sales bandwidth.
• Outsource non-core functions: Hire freelancers or agencies for tasks like accounting, bookkeeping or social media management.

Efficiency:

• Develop sales templates: Create pre-written email formats, proposals and presentations to save time and ensure consistency.
• Automate repetitive tasks: Leverage email scheduling tools, autoresponders and calendar management software to automate repetitive processes.
• Embrace batching: Group similar tasks together (e.g., all customer calls in the afternoon) to minimize context switching and maximize efficiency.

Remember:

• Don’t spread yourself too thin: Delegate, automate and prioritize to avoid burnout.
• Communicate effectively: Set clear expectations with yourself and colleagues regarding roles and responsibilities.
• Measure and adapt: Track your time usage and analyze how well your balancing act works. Iterate and adjust your strategy as needed.

A quick example: Freshworks, a B2B SaaS company, adopted a “no heroes” culture where every founder took responsibility for sales at the start. However, as they scaled, they delegated and built a specialized sales team while the founders focused on product development and strategic initiatives.

How does founder-led sales impact brand reputation building?

When founders are directly involved in sales, they bring a unique blend of passion, in-depth product knowledge and a deep understanding of the company’s vision. This direct engagement not only demonstrates commitment to potential clients but also ensures that the core values and ethos of the brand are communicated effectively. Founders, with their personal stories and dedication, build trust and authenticity in ways that traditional sales methods may not.

This approach builds meaningful customer relationships and a stronger brand identity. Moreover, founder-led sales provide valuable firsthand customer feedback, which can drive better product development and customer service strategies, further solidifying the brand’s reputation in the market.

Imran Selimkhanov

Imran is the founder and CEO of Productive Shop. He writes on B2B demand generation and SEO strategy topics to help startups understand how to win digital share of voice. Prior to Productive Shop, Imran led demand generation at an Oracle consultancy, ran an e-commerce site servicing LE teams and helped build PMO offices at technology startup companies. When he’s not at work, Imran can be spotted hiking in the Rockies, honing his clay shooting skills and tumbling off of black diamond ski tracks due to overconfidence in his skiing abilities.