B2B SaaS Sales – How to Break into the Big Leagues

Illustration of a woman in a SaaS sales role, presenting technology solutions.

Breaking into Business-to-Business Software-as-a-Service sales, otherwise known as B2B SaaS sales, seems like the holy grail to many sales professionals.

But how do you transition into an industry that seems so technical and ever-evolving, especially if you have limited experience?

Despite the seemingly insurmountable challenges, it’s an appealing and glamorous place you should want to be. The bottom line is that if you are called to it, I recommend you find a way in.

The potential rewards are huge – both in terms of personal growth along with financial success.

Illustration of cash flying through the air.

However, transitioning successfully requires strategy, research, perseverance, and of course, some helpful tips!

What is B2B SaaS Sales?

Unlike traditional software sales, where software is purchased and installed on-premises, SaaS operates on a subscription-based model, where users access the software over the internet.

SaaS vendors love the model due to the annual recurring revenue ARR, or monthly recurring revenue MRR model.

If vendors do a good job with product and client support, the customer lifetime value of deals is also significantly better with this model vs. traditional on-premises.

Illustration of a happy customer service person helping a happy customer.

The B2B SaaS sales cycle often begins with identifying potential opportunities through targeted marketing efforts that result in inbound leads, as well as cold outreach, referrals, or networking.

Once leads are generated, the SaaS sales team engages in a consultative sales process, understanding the prospect’s pain points, business objectives, and requirements.

The best enterprise sales reps will also bring added insights and perspectives into the sale, to help educate prospects on pain or benefits they may not have been aware of.

During the SaaS sales process, customized demos, free trials, and proof-of-concept implementations are common strategies to showcase the solution’s capabilities and user experience.

The B2B SaaS sales process also involves addressing technical and security concerns that businesses may have, ensuring data privacy and seamless integration with existing systems.

Sales negotiations in B2B SaaS often revolve around subscription pricing models, contract terms, scalability options, and any additional services such as training, onboarding, or support. 

The sales team plays a crucial role in building relationships of trust with potential customers, providing transparent information and addressing objections and questions as they arise.

Illustration of 2 men shaking after closing a SaaS sales deal.

After the sale is closed, the focus shifts to customer success and ongoing relationship management to retain the customer long-term and continue to upsell via the account management sales process. 

Transitioning into the Big Leagues

Moving from selling less complex and abstract products to B2B SaaS isn’t easy, but it’s absolutely doable.

Any complex enterprise sales experience is helpful, but frankly, even success in a transactional sales model, or B2C (business to customer) SaaS sales model will be applicable.

And rest assured, if you don’t have any SaaS or tech sales experience, just proven results and some confidence should get you in the door!

Let’s get into the 8 tips for how to break in to a SaaS sales team and be successful:

1. Experience Helps (but isn’t Mandatory)

In the competitive landscape of SaaS sales, having prior experience can be a significant asset.

Nonetheless, prior experience isn’t necessary for getting in or doing well in this domain.

A plethora of successful SaaS sales reps have commenced their journey without any preceding experience selling software products.

The Significance of Prior Sales Experience

Sales skills are somewhat transferable across industries and product types.

Illustration of a man selling a red car.

If you’ve demonstrated proficiency in selling other commodities or services before, those competencies will undoubtedly prove beneficial when venturing into the realm of SaaS sales too.

However, there’s something distinct about the SaaS sales process.

Depending on the Saas application you are selling, it may require comprehension of technical concepts and the ability to explain them clearly, particularly for non-tech-savvy potential customers.

Image of a person connecting some concepts on a whiteboard.

You’ll have to get comfortable learning software products and being able to show them off. This isn’t the same as selling a tangible product like a truck or widget!

Illustration of a persons hand directing us towards a computer screen, as they explain different elements of the software.

Your Entry Point Matters

If you’re earlier in your career and eager to cut your teeth in this dynamic world, consider starting in an entry-level role such as a Sales Development Representative (SDR).

These positions provide vital training opportunities where you’ll learn about the company sales approach and process while getting familiarized with your company’s solutions.

Perform well in an entry-level role and you should be on the path towards an intermediate role like Inside Sales, and more advanced roles like Outside Sales or Account Management.

Transferable Skills for Breaking In

Key skills that bode well for someone transitioning into SaaS sales include communication, deep listening, interpreting, problem-solving, and the ability to learn complex details quickly including about products, customers, and industries. 

A degree of technical aptitude is helpful, as well as strong typing skills, organization, and time management. The ability to focus and shut out distractions is also important, as is adaptability.

Remember that every bit counts on the path toward becoming a successful SaaS sales rep, regardless of whether one starts off at the beginning or as a seasoned veteran.

2. Choosing the Right Job Level

The landscape of SaaS sales is diverse, with roles ranging from entry-level to senior positions. Each level carries its own unique set of expectations and responsibilities that align with different stages of a professional’s career journey.

Finding Your Footing: Entry-Level Roles

If you’re just dipping your toe into the vast SaaS sales pool, an entry-level role could be your perfect starting point.

Positions such as Sales Development Representative (SDR) or appointment setter typically require between zero and 2 years of experience and offer a valuable introduction to key concepts like software products, customer acquisition cost, and other critical elements for success within this industry.

Climbing Upwards: Mid-Level Roles

If you’ve navigated through your initial years successfully, particularly if you’ve had a mid-level or senior-level role in a different industry, you’ll be qualified for mid-level SaaS sales jobs.

Illustration of a man on a headset sitting at a computer.

These include titles like Inside Sales, Account Executive, or Customer Success Manager where individuals are tasked not only with maintaining client relationships but also working towards achieving business goals such as increasing revenue while reducing customer churn rates.

A Quick Note About Transferable Experience:

Your past experiences can play an important role when considering the appropriate job level for breaking into B2B Saas Sales.

If you’ve worked previously in B2B or technology consulting sales, these experiences may be highly valued by hiring managers at SaaS companies.

You’re in sales, if you can spin your experience to gain access to higher quality and higher paying jobs, go for it.

Summiting The Mountain: Senior-Level Roles

If you’ve moved up the ranks in SaaS or other technology or consulting sales (say, 5+ years of successful experience), you may be qualified for senior-level SaaS sales roles.

Illustration of a woman sitting at her work desk.

Remember though, there are rarely hard rules in sales. If you’ve crushed before and can position your success effectively with a SaaS company, you can potentially land a senior role.

The thing with senior roles is that they are critical to a company’s success, sustainability, and growth. Also, sales executives are under a lot of pressure to build high-performing teams, so often they want to see related experience and success.

For example, if you are applying to sell an HR SaaS solution, a VP of Sales will likely want to see candidates with successful front-office SaaS sales experience in a similar role. 

Again, depending on circumstances this won’t always be the case, but be prepared to take a lower-level job if you don’t match up with senior roles at your preferred companies.

My advice to any aspiring SaaS salesperson is to get your foot in the door and step up your game to get your shot at a bigger job.

3. Identify the Right Size of Company

In your SaaS sales journey, it’s important to consider which size company aligns with your career goals and personal preferences.

This decision will significantly impact your work satisfaction, and either support or hinder your development.

The SaaS Startup

Startups typically offer a fast growing and dynamic environment with more flexibility than established companies. 

Illustration of a rocket ship blasting out a laptop, implying a fast growing software startup.

You may find yourself juggling multiple roles due to limited staffing – this can provide an invaluable experience as you gain exposure to various aspects of the business beyond just sales.

You may find yourself defining your own SaaS sales process, including determining what discovery process to follow and questions to ask. 

Resources for training or guidance might be scarce compared to larger organizations, and the pressure to survive will be a constant theme in the company culture.

Larger Established Companies: A Different Ball Game

If stability appeals more than risk-taking does, consider an established company that is out of the early-stage startup hustle.

These businesses are generally considered safer bets when it comes to job security and company health, and their operations and customers are more globally distributed.

Illustration of a computer crunching and sorting data from all around the world.

Onboarding programs at established companies are usually well-defined, easing new hires into their roles while providing ongoing support through structured training and mentorship.

The drawback to large companies is that you will be a small fish in a big pond, with less impact and influence at the highest levels of the company.

Your contributions will be diluted across a larger sales organization, meaning a less meaningful contribution overall.

Larger organizations are less scrappy and more process-oriented, so depending on your personality, preferences, and goals, you should know if an earlier or later-stage company environment is better for you.

4. Vertical or Horizontal Focus?

An important initial question to ask yourself is, are you interested in selling into a specific vertical market or are you less interested in the customer market?

If for example, you have strong knowledge and a deep network of contacts in healthcare, manufacturing, or another field, perhaps you’ll want to sell SaaS applications into that market.

The alternative is to choose a product with broader appeal across multiple markets. Let’s examine these two paths in more detail.

Vertical Specific Solutions

If you’re leaning towards selling vertically, it means focusing on specific markets. An example would be healthcare providers needing tailored CRM or billing systems.

Illustration of a female doctor on a tablet.

This approach allows you to gain a deep understanding of customers’ needs and enables customization that aligns perfectly with the market’s unique challenges.

It often results in higher conversion rates due to potential customers recognizing the value in software built specifically for them.

The flip side is that this method requires extensive knowledge about the sector including its terminology, organization structures, and business drivers.

Illustration of a hospital.

Also, with a smaller total pool of prospects, there is less addressable market.

Horizontal Strategy

Selling horizontally implies offering products across a wide range of industries; think of broadly applicable project management tools used by businesses from construction firms to digital marketing agencies.

The key advantage here is the expansive reach, increasing revenue opportunities through a larger pool of prospective clients.

This broad spectrum approach does come with associated risks, though, including heightened competition and less ability to differentiate.

Many SaaS companies choose this route due to the scalability aspect, but often over time become more vertically focused as they grow and begin winning more business in specific areas.

Making Your Decision

There is no right or wrong answer. If you have interest, expertise, and/or contacts in a particular vertical market, you may enjoy focusing on it.

If you don’t and are curious to see what markets may be interesting to you, consider horizontal solutions.

Perhaps your ideal company has a particular market focus, so that may be the deciding factor.

Personally, I’ve sold products and solutions horizontally and have made a fine career out of that approach, but I know plenty of highly successful colleagues that have zeroed in on a particular vertical and found great success.

5. Choose Your SaaS Application Pathway

Selling SaaS products requires a strong understanding and interest in what you’re offering.

This is especially true when dealing with complex applications that demand comprehensive knowledge to effectively convey their benefits.

The universe of SaaS includes countless solutions with broad industry applications, plus plenty of vertical-specific solutions.

Let’s have a closer look at the applications and options you’ll want to consider.

SaaS Applications Big List

There are endless interesting SaaS applications out there, and all sorts of sub-categories. Here is a big list of some of the larger, main categories:

Customer Relationship Management (CRM) – CRM software helps businesses manage interactions with customers and potential customers, enabling them to track sales leads, customer information, communication history, and improve customer engagement.

Help Desk, Customer Support and TicketingHelp desk software facilitates customer support by managing and tracking customer inquiries, issues, and requests, leading to improved customer satisfaction.

Call Center – Call center software streamlines customer interactions by providing tools for managing incoming and outgoing calls, call routing, agent performance tracking, and customer information access.

Illustration of a man on a headset, working in a call center.

Enterprise Resource Planning (ERP)ERP systems integrate various business processes like finance, human resources, inventory, and procurement into a single platform, improving efficiency and coordination across an organization.

Human Resources Information Systems / Human Resources Management (HRIS/HRM)These tools streamline HR tasks such as employee onboarding, payroll, benefits administration, and performance management, helping organizations manage their workforce effectively.

Supply Chain Management (SCM) & LogisticsSCM software aids in optimizing the movement of goods, materials, and information throughout the supply chain, enhancing coordination among suppliers, manufacturers, distributors, and retailers.

Illustration of a globe with different forms of supply chain transportation beside it.

Project Management Project management tools assist teams in planning, executing, and monitoring projects, facilitating collaboration, task tracking, and timeline management.

Communication Tools These platforms include messaging, video conferencing, and collaboration tools that enhance team communication and productivity, especially in remote or distributed work settings.

Finance & Accounting Finance and accounting software streamlines financial processes such as budgeting, invoicing, expense tracking, and financial reporting, improving accuracy and financial management.

Illustration of an accounting spreadsheet on a computer monitor.

Legal and ComplianceThis category would encompass SaaS platforms designed to help businesses manage legal processes, compliance requirements, contracts, and legal documentation.

Illustration of a compliance checklist on a computer screen.

Marketing Automation – Marketing automation platforms enable businesses to automate repetitive marketing tasks, including email campaigns, lead nurturing, and customer segmentation.

Analytics & Business Intelligence These solutions collect, analyze, and visualize data to provide insights into business performance, aiding in data-driven decision-making.

e-Learning & Traininge-Learning platforms offer tools to create, deliver, and manage online training and educational content, making employee training more accessible and efficient.

Illustration of online learning on a computer screen.

Content Management – Content management systems (CMS) help businesses create, organize, and publish digital content, making it easier to manage websites, blogs, and other online platforms.

e-Commercee-Commerce platforms provide tools for creating and managing online stores, enabling businesses to sell products and services over the internet.

Illustration of an e-commerce transaction happening over 2 computers.

Retail and Inventory Management – Platforms that assist retailers in managing inventory, sales, and online sales.

Real Estate & Property Management Real estate solutions include property management, transactions, and marketing, optimizing real estate operations and sales processes. Property management software assists in managing rental properties, leases, maintenance requests, and tenant interactions.

Illustration of a house hovering above a mans hand that is sticking out of a computer screen, implying real-estate software.

Healthcare ManagementSolutions tailored for managing patient records, medical billing, appointment scheduling, and other healthcare-related tasks.

Manufacturing and ProductionSolutions designed to optimize manufacturing processes, production schedules, and quality control.

Illustration of a manufacturing factory with a truck in front of it.

Event Management Platforms that assist in planning, promoting, and managing events, conferences, and seminars.

Travel and Hospitality ManagementSolutions designed for managing bookings, reservations, and customer interactions in the travel and hospitality industry.

Membership and Subscription Management – Platforms that help businesses manage memberships, subscriptions, and recurring billing for products and services.

Nonprofit and Fundraising – Solutions tailored for nonprofit organizations to manage fundraising campaigns, donor relationships, and other nonprofit-specific needs.

Illustration of a man putting cash in a donation box being held by a woman.

Field Service Management – Platforms that assist in managing field operations, service scheduling, and dispatching for businesses with field service teams.

Cybersecurity and Data Protection – This category includes solutions that offer cybersecurity, data protection, encryption, and other related services to safeguard digital assets.

Illustration of a man on a computer with a a large security icon.

Other Considerations

Beyond your personal preferences, be sure to also consider current market trends in the cloud-based software industry, when making decisions about where to find saas sales work.

For instance, marketing automation tools saw tremendous growth in the late 2010’s due to increasing digital marketing demands by businesses worldwide. e-Learning was very popular during the pandemic as companies needed to move training online.

Assessing trends will help you uncover potential opportunities available in different segments of the SaaS market. Ultimately that will lead to sub-categories with higher chances of success both now and in the future.

6. Identify Ideal Companies

Now that you’ve drilled down and identified a few SaaS applications you’re interested in, it’s time to build a list of potential employers to approach.

Identify and research as many companies as possible. There may be a couple that really stand out for you, but find as many suitable targets as possible and push hard to turn them into genuine opportunities.

I like to poke around websites, review product & solution pages, executive bios and backgrounds on LinkedIn, and also leverage tools like Glassdoor to get inside information direct from current and former employees.

Remember to stick to the company sizes you are most interested in.

Evaluating Opportunities Within Each Company

To give yourself the best chance of success in the right situation, take the time to realistically evaluate each opportunity you find.

Does the role match your experience level? It’s ok to be a little under or over-qualified, but ensure it’s not a left-field situation.

Does the role sound interesting and fun to you? Is there room for the type of career growth you are looking for?

It’s important to get a sense for the long-term progression paths offered by the company – does it align with your personal and professional aspirations?

Research and reflection aren’t always fun, but landing your ideal gig is worth the extra effort and patience.

Making Connections With Key Players

As a sales professional, it’s your responsibility to show the commitment towards securing your preferred outcome, so go the extra mile in landing your ideal job.

Find sales and hiring managers through LinkedIn and reach out directly. Call in and express your interest. At the very least, ensure an extremely concise, clear and persuasive resume and cover letter.

Illustration of a business man on a mountain using binoculars, implying that he's looking for a hiring manager so he can get a job.

If you want it, figure out how to persuade the right people and then be unrelenting in your pursuit. For more ideas, check out this article.

7. Master Your SaaS Sales Offerings

If you want to outperform average SaaS sales reps, mastering your solutions and resources is a prerequisite.

It’s not just about knowing what each feature does, it’s understanding how those features can be applied to solve real-world problems for your prospect, whatever industry they may be in.

Dig into Product Knowledge

Achieving expertise on your products and solutions is a great way to differentiate from reps that believe their value is mostly in their sales skills and ability to manage a complex SaaS sales model.

As previously mentioned, the larger your employer the more likely there is to be solid product and sales process training as a part of onboarding.

However, if you want to be exceptional, you need to go extra lengths to deepen your knowledge.

Learn as much as you can about products, services, bundles and historical deals.

Pay close attention during live or recorded product demos and training sessions led by development teams or product managers within your company.

More helpful hints:

  1. Become an active participant during internal training sessions.
  2. Review recent historical release notes so you can see the evolving product roadmap, to get a sense for how the market is evolving.
  3. Sign up for industry newsletters and track the top analysts in your space, to learn about broader trends and new developments with your competition.

Go Deeper with Your People

Commit to mastery by going beyond resources and tools. That means leveraging all the human capital resources that are available to you… put another way, all your amazing and skilled colleagues across various departments!

Illustration of colleagues on a computer screen.

Regular interaction with other departments such as marketing, client success, and product, will provide valuable insights that will increase your understanding and improve your pitches over time.

Maintain healthy relationships throughout various levels inside your organization as well, including management hierarchies.

Especially in larger company environments, managers that are a few levels up will have insight into strategy and goals that may not be top of mind where you sit.

Sales Enablement – The Unsung Heroes of SaaS Sales Teams

Lean start-ups won’t have these resources, but once you get beyond the start-up level you may have the good fortune to work with high quality sales enablement professionals.

These folks do everything from analyze sales data to recommend processes that better capture and leverage that data.

Expect solid ideas for pipeline management best practices, and tools that can be used to make your job easier, and the entire sales department more effective.

They often have deep industry insights and can liaise with marketing to ensure clear lines of communication between these related departments.

Often salespeople resist outside influence, but when done right, sales enablement is there to do just that – enable more sales!

Don’t overlook or downplay the impact these teams can have to help the company achieve it’s lofty goals.

8. Don’t Forget to Master Yourself

The journey from your starting point in SaaS sales to a level of mastery is really dependent on one thing, and that is your degree of personal investment and commitment.

Everything that will lead to your success is impacted by the degree of your willingness and endeavor to push, learn, apply and grow.

Illustration of a man sitting on a pile of books, reading.

The Secret to Sales Success isn’t complex, but it is hard and sometimes painful work. 

Commit today to being a professional, and doing what needs to be done regardless of your mood or motivation levels.

Ensure Your Personal Foundation is Solid

Your foundation includes clarity about your desires and motivations. Have you ever honestly considered what you are truly motivated by? If not, or if you think things may have changed, follow this process.

Next, take the time to examine your beliefs and values. Are your beliefs supporting you? They aren’t issued at birth, they are developed over time.

As for your values, have you identified them? They govern your behavior, so it’s a good idea to know them.

Acknowledge Your Strengths and Weaknesses

To master yourself in any profession, including being a successful SaaS sales rep, you must understand your strengths and weaknesses. This insight will enable you to maximize your potential while giving you clarity on areas that could use enhancement.

I’m a big believer in working on your weaknesses if they can contribute to your overall success and satisfaction, so knowing what they are is the starting point.

You can use various tools such as Gallup’s CliftonStrengths assessment or even perform a simple SWOT analysis on yourself to gain this critical knowledge about who you are as both an individual and professional.

Cultivating Emotional Intelligence (EQ)

Sales professionals with high emotional intelligence (EQ) are adept and understanding and truly empathizing with client needs and emotions, leading to more authentic interactions, better relationships, and more sales.

Cultivate your emotional intelligence by intentionally become more self-aware of your behaviors, communication styles and emotions, and observing how others react and are affected by you.

Practice mindfulness, considering meditating to calm and control your mind, seek honest feedback from others, and be thoughtful about how you interact.

Implement Effective Personal Habits

Your habits play the crucial role in what your future will become.

If you want to master sales, SaaS, or any demand that requires effort to improve, you need to create the right daily habit blueprint that will lead to your desired outcomes.

Remember, anything lucrative is going to involve fierce competition. You’ll experience this with both your colleagues and your competitors in the field.

Commit to professional growth, but understand that your personal habits are equally as important.

Real success in this life is across the board, and since everything is a byproduct of habits, make the investment and commitment to do the right daily actions in every area of your life.

This means a workout regimen, good eating habits, enough rest, and of course a fierce work ethic and growth plan.

Illustration of a woman working out on a yoga mat.

I’ve tried every method for dialing in my habits, and found the most effective strategy is to have an ultra clear “why”.

What finally got me to implement all the habits I operate with today, was having a clear vision of the total person I admired and wanted to become. Find your “why” and be unrelenting in your pursuit.

“Atomic Habits” by James Clear offers great insight on this topic.

B2B SaaS Sales FAQs

Is SaaS sales difficult compared to other types of sales?

I’ve sold different things in my career, and I would say “yes”, SaaS solutions are more complex to learn and master than most other products.

But rest assured, if you are committed to learning and to your success, you can figure out SaaS applications and how to sell them.

Is SaaS sales a growing industry?

When you think about it, software really does make the world run and operate smoothly. 

Software as a service is the most popular delivery model for software, so yes, SaaS sales is a growing industry that won’t be going away anytime soon.

Is SaaS sales lucrative for sales reps?

Extremely successful SaaS sales reps are some of the highest paid salespeople on the planet.

In most cases, comp plans feature a base salary, commissions based on performance, plus solid benefits.

Illustration of a bag of money.

Do SaaS sales reps need a degree?

One of the great things about sales is that your ability is what gets you paid.

Certainly there are some companies that will demand a degree even for their sales people, but many will not.

Relevant degrees include marketing, psychology, business of course, or for technical sales roles like sales engineers, a computer science degree is helpful.

Illustration of a man pointing to his degree on the wall.


Transitioning into SaaS sales is a journey of strategy, research, and determination.

Leveraging your existing knowledge and results in sales can be a great advantage, yet it’s not the only path to success.

You’ve learned about targeting the right job level based on your experience and skills.

The size of the company matters too – startups for less structure, and big companies for more support.

Identifying SaaS applications you’re passionate about will make selling them more satisfying.

Find ideal companies that align with this passion; then it’s all about getting noticed by their sales and hiring managers.

Mastery doesn’t stop at solutions and resources; mastering yourself is crucial too.

Your Next Steps

Are you ready to break in and become a SaaS sales rep? Do you want to crush targets and earn like a boss? Let me show you the way to success in SaaS sales.

Join my program for advanced SaaS sales, where I provide helpful content designed specifically for people like you who are eager to succeed in SaaS sales.

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