How to develop your tech sales career

In a recent webinar, Alex Gasson, CEO of Delta-v, shared practical insights on building a successful career in B2B tech sales.

He unpacked how to get into tech, where to focus to build experience, and the career mistakes that could hold you back.

Why work in sales?

(4:51)

If you’re looking at sales in the context of saying “I want to go and work in tech”, then there are broadly two paths that you can go down.

Firstly, the product path, where you are potentially a developer or a product manager, or a designer, and you’re involved in the creation of the product.

The other path is go-to-market, where you’re taking the solutions to market and getting them sold.

Tech companies usually start out product-focused, with most of the organisation centred on developers. But as they grow, the focus shifts to go-to-market. Large B2B software companies generally have much bigger sales teams than tech teams because the focus is on distribution and selling.

So, you’re either on the technical side or you’re on the go-to-market side, which is really marketing and sales. If you want to work in tech and you’re not technical, sales and marketing is the route for you. And then sales is one of those specific options.

Why choose a career in sales?

• Build and grow companies. If you choose a career in sales, what you are doing is playing a key role in building and growing businesses, because if people are not giving you money, you don’t have a business.
• You learn about people, companies, and markets
• You find and provide solutions for complex problems
• You’re developing a scarce skill set.

“I’ve been on calls with CEO networks and they’ll say, ‘Sheesh, I thought finding developers was hard until I started trying to find good salespeople,” says Alex.

• You can see your direct impact – like signing a new client, etc.
• Out-earn your peers. Sales is a lot of hard grind, and the payoff for that is that you should be making really good money. A good salesperson should be out-earning most of their peers.
• Lead business units & companies. Your starting point might be being an individual contributor, but over time you can ultimately get to the point where you are leading business divisions or entire business units through a career in sales.

Why not to choose a career in sales

One of the things people don’t like about sales is the accountability, because it’s normally very clear if you’re winning or losing.

Either you’re closing deals or you’re not. Either you’re hitting target or you’re not.

If you’re not comfortable with that, then you probably don’t want to have a career in sales.

Understanding the sales landscape

(12:58)

Let’s unpack the spectrum of complexity in sales.

Types of sales

Transactional sales: This is where a company is selling a simple and well-understood product. Generally, this also aligns with low deal sizes, high volumes, and short sales cycles.

Typically, you’d be selling to individuals, small businesses, and possibly mid-market. A low deal size would be anywhere below say R150,000 or about $7,500.

Complex sales: Here you’re selling complicated products with large deal sizes, lower volume, and long sales cycles.

You’re selling into mid-market or large enterprise organisations. A complicated product could be a payment system, an accounting system, or a tax calculation engine.

Deal sizes could be anywhere from $30,000 up to hundreds of thousands of dollars.

You close fewer deals, but sales cycles are long (6 – 24 months) because the products are complex and buying decisions are big.

The types of organisations you’re selling to in enterprise would be companies like MTN, Shoprite, FNB, and the big banks. In that world, to make the sale you have to navigate a very complicated buying journey and deal with many stakeholders along the way.

Types of solutions

A vertical solution is sold into a very specific industry. For instance, an e-commerce payment gateway that online businesses use to accept payments.

These are generally less competitive because they require deep domain knowledge, but the addressable market is often smaller

Horizontal solutions are sold across a range of businesses, but into a specific business function. For instance, selling accounting systems into a finance team or selling marketing automation like HubSpot into marketing teams.

Generally, these companies face a high degree of competition, so it can be harder to make sales. The advantage is a much larger addressable market because you can sell to many businesses. You also need to sell more volume because the unit cost is lower.

When you are picking a role, it’s important to understand the dynamics around this and figure out: am I selling a vertical solution? Am I selling a horizontal solution? And what are the implications for my ability to be successful and to sell?

The SDR role

(18:34)

If you’re building a career in sales, the entry point into most sales organisations, particularly in tech, is going to be the Sales Development Representative (SDR) role.

It’s a great place to start your career because you develop some fundamental skills that are essential for being an elite seller.

“In many cases, the SDR role has a bit of a bad rep, with people thinking it’s very low level, very entry level. It is fundamentally one of the most important roles in the sales organisation, because if you don’t have sales opportunities, you don’t have anything to close,”

What you get out of being an SDR

Pipeline generation 

This is a skill that only elite sellers possess. It is a fundamental skill that anybody who is a top seller earning millions of rand a year has developed, and probably only 8 to 10% of people in sales are actually good at pipeline generation.

Rapid learning and skills development

SDRs perform a high-volume role in the sense that they’re reaching out to a lot of people, making a lot of calls, and having a lot of interactions.

You rapidly learn communication, research, discovery, objection handling, and how to close. You’re not necessarily closing deals, but you are getting people to part with their time in exchange for you showing them your product/service.

You also earn persistence, resilience, and how to manage stakeholders.

Specialist knowledge

In an SDR role you are taking a product or service to market, so you develop industry-specific and market-specific knowledge, for example, learning how the banking sector operates when selling financial technology.

Messaging

You get exposure to and learn about messaging – what works, what doesn’t – which is critical for sales and marketing.

Technology

You learn about sales automation technology and how to use it.

Track record

If you have a consistent record of performance, of hitting your target, that is something you can carry across roles. It creates huge credibility with any employer.

Where can you go from being an SDR?

(28:00)

See possible career paths, mapped out here.

Managing your sales career – what to do

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• Create a track record: In sales, you live and die by your track record. Two things to think about here:
  • Spend sufficient time in a role so that you create a track record of career stability.
  • Build up a track record of meeting and exceeding targets and doing that consistently.
• Take advantage of opportunities. The longer you spend with a company, the better you are positioned to take opportunities (leadership and otherwise) when they come.
• Focus. When you start working in a particular industry, you often develop valuable specialist skills and knowledge related to that domain or vertical, or even working on a specific type of deal size.

“We had someone in our business who was super successful as an SDR. He was working on a customer of ours selling very complex financial technology into the world’s largest organisations – the biggest banks, retailers, telcos. When he left our business, he went to work for a company that sold marketing automation solutions to 15- to 20-person startups.

“He threw away all that knowledge he had developed around fintech, all that knowledge about selling into very large, complex organisations, and all that knowledge about working on deals worth millions or tens of millions of rand,”

• Choose the right companies. A lot of companies, in tech particularly, do a great job of marketing themselves as a great place to work. But be sure to test this, and do your research to see what’s really going on.
• Experienced leadership. You want to be in businesses with established, experienced leaders – especially early in your career – who you can learn from and who will accelerate your career.
• Product-market-sales-fit. Make sure you work for a company who has product–market fit and an established sales process. That makes your life much easier as a salesperson, because you can execute on a well-understood process instead of figuring it all out yourself.
• Company DNA and ways of working. If you go and work for a great business, you learn the right behaviours that are ingrained into the way the business operates.
• Market size & opportunity. Is there actually a big enough market to sell into? For example, if you are selling big banking solutions into South Africa, there are only five or six banks you can sell to.
• Brand. Lastly, something that makes your life a lot easier is if a company has a great brand or strong brand awareness. You have materially different conversations when companies trust you because of that brand.

Managing your career in sales – common mistakes

(41:35)

Job hopping

If you are hopping jobs, your CV looks bad, and many companies won’t consider you without sufficient tenure.

Throwing away valuable skills and knowledge

Be deliberate when moving companies: are you building on the skill set and knowledge you’ve already created? Or are you throwing all of that away?

Picking the wrong companies

• Make sure they have product–market–sales fit
• Avoid immature sales leaders
• Avoid selling products that are hard to sell

Selecting the right role for the right life stage

Think about buying behaviour. Somebody in a bank who is in their 50s or 60s is at a very specific life stage. Who are they going to trust? Are they going to trust a 25-year-old to sell them a R2 million piece of software? These are things to consider.

Opportunities open up over time if you build trust in an organisation. Spend time in role, focus, and position yourself well, and you will go far in your sales career.