Who Is This Blog For?

As the title hints, this blog is dedicated for recent college graduates or other individuals who are in their career in any stage who is considering a career change. Should you consider software sales?

What this blog truly communicates to, is me, well the past MrAddOil who just graduated from university about 3 years ago.

I want to paint a holistic picture of what this career trajectory entails, the pros and cons, and other insights that you might not get from other blogs (generated from software companies for the sole purpose of recruiting).

Based on demand or request, I might produce follow up blogs that digs deeper into specific topics mentioned in this all-encompassing post.

Lastly, I hope from this blog, you can make a solid decision on whether want to consider this path.

My Background & Story Time

I love story time. So for me, I am a humanities college graduate, that graduated in with 2 degrees in philosophy and linguistics. The best, most lucrative degrees to pursue…That was sarcasm by the way. You can kinda see where the tone of this is progressing towards…

Nevertheless, do I have regret? Yes I do, HOWEVER, I have strong confidence that in the future, I will look back maybe 5, 10 years from now and reflect upon my university decisions and be proud of my younger self.

Why? Because like what my mentor said, “you get to say you studied and did what you liked in university and not a lot of people can say that”. There are pros and cons with this statement, but I will learn to view this from a positive light.

What’s more, during my university year, I had the privilege of studying abroad to find my roots (traveled to 25+ cities in China, study in Nanjing, and intern in Shenzhen), traveled the world, perform live music, and compete as a breakdancer with my crew Jive City (previously Boogie City Resident).  In short, my university years was really an enriching, fulfilling experience.

But guess what? The real world doesn’t care about personal growth, etc. Reality hit hard for me late 2015, early 2016. I wasn’t qualified for the majority of decent paying jobs that can afford me to sustain myself in expensive San Francisco, where the annual cost of living for a single person is projected at $43,581 or $3,652 a month.

This is where I happened upon the world of SaaS Sales.

What Is a SaaS Sales Career?

Here’s a good resource from HubSpot: SaaS Sales: The Ultimate Guide on this definition.

I don’t want to be bite (breakdance slang for copying), but I will use the same structure as the HubSpot guideline and fill in gaps as I see fit based on my own rendition.

(1) What is SaaS?

It stands for software as a service. Meaning, the main product of the business is a software that extends as a service. Think of the big tech companies like Facebook, LinkedIn, Google, etc. These businesses are great examples of SaaS.

Another popular arena where SaaS is popular is amongst start-up in silicon valley and especially in San Francisco (my hometown what what!).

(2) What is SaaS Sales?

If you ever held any role in your university years that was customer facing (cashier, retail sales associate, etc), a SaaS Sales role is similar in the sales sense but the environment is more technically oriented.

Simply, you are selling a software product as a subscription based service. That’s how the majority of tech companies, especially in the start-up scene, structure their business model.

You would be employed as an inside salesperson, meaning, you will be working an office job and interact with potential clients via video conference, email, and phone calls.

(3) What type of SaaS Sales Models Are There?

Understanding a company’s sales model is extremely important because it will dictate your day-to-day workflow and activities.

Also, you will develop different type of sales skill sets that are catered towards a specific niche model.


Self-service SaaS business models involves allowing prospective customers with free trials or freemium accounts. In other words, the majority of leads are inbound.

These business models are normally B2C or purely consumer facing products (i.e. Spotify, Medium, or a simple example like a phone plan). Typically the ASP (average sales price) is low, which allows for this type of model.

Again, HubSpot does a killer job in being the leader in inbound sales because they were early pioneers of creating the inbound sales methodology via implementing great marketing practices.

Salespersons in these orgs have the opportunity to do full-cycle sales, which I would argue is probably the best place to start your sales career if given the option or choice. I’ll explain later in this blog post why this makes a lot sense for people new to sales.  

Here is a blog from Lucidchart that describes the 7 stages of a typical sales cycle. With inbound-full-cycle-sales, stage 1 to 2 has already been done for you. Therefore, you start at stage 3 (lead qualification) to stage 7 (asking for referrals).

Transactional Sales

The gist of this means that the sales cycles are really short. Think 1 call 1 close type of sales engagements. One influencer that comes to mind would be Dan Lok, who has been given the title of “King of High Ticket Sales”.

In Dan’s teachings, he stands behind finding a sales role that is a pure closing role where an influencer or a business does the pre-work (lead generation, lead qualification, etc) and when leads land in your pipeline, they are in the end of the funnel and ready to buy after a final, human conversation.

In a similar sense, software companies employ salespersons to reach out to SMB (small, mid business) business owners or accounts to close deals that can range from $200 to under $10,000, where the latter price would be more rare.

Transactional sales roles are quite correlated with a company that has an inbound lead generation type of business model.  

Mid-Market Sales

The sales cycles for this segment are in-between 3-6 months. I believe this is the happy balance between transactional, SMB sales and enterprise sales.

Typically, decent sales reps in this segment can make a minimum of $100,000/year and up to $200,000 for top performers who are able to sell into pseudo-enterprise deals.

The risk and reward scale is much more balanced here.

Enterprise Sales

Every salesperson, if they have not been burnt out of sales or has been successful in their sales career, wants to get into enterprise sales.

This is type of sales model involves targeting Fortune 1000 to 100 companies, longer sales cycles between 6 – 12 months, and complex sales process (multiple stakeholders, negotiations, product requirements, etc).

Enterprise sales is the most lucrative of the sales model of the three we’ve mentioned. This is a legit way to become rich since enterprise sales reps normally make a minimum of $250,000 per year, average around $500,000 for mid-level performers, and up to $1,000,000 for exceptional performers.

Yet, enterprise sales is the most stressful of the bunch because it’s a high-risk, high-reward type of role.

What is The Typical SaaS Sales Career Progression?

Rainmakers has a great blog that outlines the typical sales roles and their salaries. Below is my interpretation of these roles based on my experience and observations.

New Business Sales (Hunter)

These type of sales role belong to the new business side of a company. The advantages of these type of role are: higher pay, relatively easier to get into, and fast growth if your performance is high.

The disadvantage of being a “hunter” on the need business side: more stressful because you are carrying new business quota, easy in so easy out – higher turnover, and your success is dependent on the demand for the product and the territory you are assigned.

Difficulty, pay-rate in this category differs based on which market segment. This will also apply for the other “farmer” sales category. Salary, sales engagement, and difficulty will range based on the market tiers. Here is a quick breakdown:

Salary Grade

Small Business Level

Small Business Market Segment
  1. Expect small e-commerce businesses
  2. Small, “just gave birth” or “pregnant” start-ups with just 1-3 co-founders
Small Business Sales Cycle
  1. It can range from 1 call close to 2 weeks depending on the quality and maturity of a given lead
Small Business Average Deal Size
  1. Deal size will range from $100 to $5000 but don’t expect anything higher than $10,000.
Small Business Sales Salary
  1. The average pay for SDRs is $50-$55,000 base
  2. Small business AEs also share the same range
  3. Small business AMs make $67,000

Mid Market Level

Mid Market Segment
  1. Small start ups with around ~50 employees and above
  2. They have at least at a minimum, Series A funding
Mid Market Sales Cycle
  1. It can range from 1 month to 3 month depending on the quality and maturity of a given lead
Mid Market Average Deal Size
  1. Deal size will range from $10,000 to $30,000 but don’t expect anything higher than $50,000.
Mid Market Sales Salary
  1. Mid market SDRs in San Francisco make ~$65,000 average
  2. Mid market AEs also make a base of $67,000
  3. Mid market AMs make a base of $67,000 on average [farmer role]

Enterprise Level

Enterprise Segment
  1. Target Fortune ### accounts, think Google, Walmart, etc
  2. Typically public companies with deep pockets
Enterprise Sales Cycle
  1. It can range from 6 month to 24 month depending on the quality and maturity of a given lead
Enterprise Average Deal Size
  1. Deal size will range from $100,000 to several $ millions or more
Enterprise Sales Salary
  1. Enterprise SDRs in San Francisco make ~$77,000 average
  2. Enterprise AEs make average $106,000 base salary
  3. Enterprise AM make an average of $86,000 base [farmer role]

That being said, let’s breakdown the typical roles in the new business category.

Sales Development Representative (SDR) [Entry-level]

This is the grunt sales role of all organizations. This role title is synonymous with business development representatives (BDR). It’s a way to get your foot in the door but you do not want to stay here. No one does.

Granted, I’ve seen individuals later on in their career who did not graduate or choose to move into a closing role (AE) and they are the rare exceptions.

What will you be doing? You are in charge of lead generation, hence, the majority of SDRs will focus on outreach in the form of cold calling, emails, conferences, etc.

The SDR role is arguably the hardest job in all organizations. It’s extremely stressful because you have to hit meeting quotas, deal with uncertainty, ambiguity, and market luck.

Because of all these factors, SDRs have the highest turnover rates of all the sales role. It’s the “easy come easy go” role.

Enterprise SDR

The majority of SDR roles are straight-up call center, telemarketer roles where if a lead is interested in a meeting, you throw a meeting on your AEs calendar.

Enterprise SDRs can argue base salaries from $60,000-$80,000, with a variable commission of $20,000-$40,000


Next, the fortunate SDR roles also have opportunities to actually qualify the leads prior to handing it over to an AE to close the deal.

*Full Sale Cycle SDR*

These are the SDRs who have the best job and I keep recommending that anyone who is considering sales as a career, to start in this role first.

You will effectively be both the SDR and AE, guiding a lead from initial contact to close. I’ll share my argument for this SDR role for new grads and career changers towards the end of this blog post.

This is the hidden thesis of this blog post.

Account Executive (AE) [Entry-Junior-level]

This is the key sales role in any organization because she is responsible for generating new business bookings, which would lead to revenue the company and keeping the lights on for everyone.

If you can and get lucky enough to land an AE role as a new college grad or career changer. Prioritize this title and role over being SDR in any situation, universe, or existence haha!

Why? All SDR roles are a grind and fight to convert into an AE, closing role. I argue, the SDR role is one of hardest job you can ever do in your life.

Therefore, it’s better to start your career off on the right foot and to set yourself up for success as an AE out of the gate.

Then again, for the individuals who want a challenge, if you can make a successful transition from SDR to AE and earn that promotion (earn is kind of a strong word, and it does not always correlate with direct hard work because it does depend on luck – being in the right place, asking at the right time, having the right boss who likes you, etc), that is something for you to be extremely proud of.

Full transparency, I did not make that cut. But that’s ok. The majority of prospective salesperson hop over to another company and get promoted to an AE role like I did.

Everyone’s path is different. Take pride in yourself and understand your value. Don’t let companies, hiring managers, or bosses tell you otherwise.

I’ve been in situations where I got an offer, but when it came to salary negotiation, one CEO pushed back and said, “you and me both know you are not worth this price”.

This is the real world and stuff like this happens. But use that anger and emotion to motivate and better yourself. Ok enough with the pep talk, back to the regular program.

SMB and Mid Market Account Executive (SMB, Mid Market-AE) [Entry-level]

If you land a role as an SMB AE for your first gig out of college or from a different career path, this is a good place to start.

This can be equivalent to a full cycle sales development representative because SMB AEs either process inbound leads to close (inbound full sales cycle) or they are in charge of an outbound full sales cycle: from prospecting, generating leads, qualifying an opportunity, negotiation, and closing business.

As for salary, what you can expect is probably a base of $50,000 to $60,000 with a variable commission. Which isn’t a bad thing especially out of the gate from university or from another field.

You will learn a lot more in an SMB AE role than an SDR role. If you seriously want to give Sales a try, try to expedite your way into this role, either interviewing into it the first time or getting promoted into it.

An SMB or mid market account executive’s salary sit around $67,225 on average.

Enterprise Account Executive (EAE) [Senior-level]

This is what you should shoot for if you want to make an average of a quarter million $$$ annually as a bottom line with explosive, lucrative earning potential up to $ million a year.

Typically, unless you graduate from an Enterprise SDR and transitioned into this role after an average of 2-3 years of grinding (I’ve seen exceptions who transitioned to an Enterprise AE role within 1 year of being SDR, but these are rare and you have to be in the right company and have the right opportunity in front of you)

I wish I knew more about this type of sales opportunity, but you can read this, “10 Step Guide to Making $1,000,000/year in Software Sales” to get an idea of the costs of being employed in such a lucrative position.

Sales Engineer (SE)

Sales engineer is an interesting role because its a hybrid role that sits between technical support and sales.

You do hold a quota, but it’s usually tied with a group of AE’s quota because your function is to support pre-sales technical demos with technical stakeholders (software engineers, product managers, technical executives, etc) when an AE cannot hold deeper, technical conversations.

I would argue this is a great role to target after you’ve landed and held an AE role for a period of time because you can develop a broader, balanced skill set composed of business and technical prowess.

Moreover, it’s a less stressful role because you don’t carry the full weight of a sales quota that an AE would normally carry. Therefore, more job security (if such a thing exists) compared to a full quota carrying sales role like an AE.

Plus, it is a more fun role because you don’t have necessarily play the function and role as a salesperson, you can leverage your identity as a technical consultant, which can help you earn more trust and break through the walls of stakeholders who are on guard against salespersons.

According to Glassdoor, Sales Engineers can make an average base of $185,000. That is not bad at all.

Post Sales Account Management: Renewal & Upsells (Farmer)

These are post sales roles that are responsible for managing the relationships of a company’s existing book of customers.

If given an opportunity to start over, I would choose a farmer type of role out of college and here are my reasons why:

  1. Less riskier and stressful: You are dealing with existing customers versus prospects. This means you don’t have to win them over and this translates to better conversations.
  2. Easier sale: It’s easier to upsell and renew existing clients vs convert a new customer.
  3. Learn more about product and business: You learn more about the company’s product because you will be troubleshooting and implementing that technology for recently converted customers and existing customers. Furthermore, you will have richer conversations with customers and understand their pain points and prescribe solutions where your product can address those issues.

The drawback of post-sales roles are as follows:

  1. Less pay: Since the role itself is less stressful than a new business sales rep, companies typically pay post sales reps less in base and commission variable.
  2. More activity: You will have more activities and responsibilities because you will own a large book of accounts and you are charged with ensuring that a specific percentage of customers renew and reduce or prevent churn.

Customer Success Associate (CSA) [Entry-level]

Being in a customer facing support role is powerful because you understand the customer pain points the most compared to anyone else in the org.

Differing from a traditional customer support rep, this role is a proactive, post sales implementationist vs pure customer support. Meaning, you will devise strategies to increase the probability of customer renewals.

Ultimately, this role is fun because its a more strategic task, plus you have opportunity to engage in the business goals and pain points of a given customer in more detail versus new business sales reps who have to earn that trust to gain disclosed information.

Customer Success Manager (CSM) [Junior-level]

The work and function of a CSM is similar to CSA. The difference is their responsibility is scaled and they are tasked with handling bigger books of customers, typically, enterprise-level clients.

CSM might also be responsible for upsell quota which bleeds into AM territory, but a CSM can bare that responsibility also or identify these opportunities for an AM to close upsell businesses.

CSM can also act in a technical role similar to a Sales Engineer on the backend because they interact with Product, Marketing, and Engineer teams more often than new business side sales rep.

Hence, they will be tasked with helping clients implement the technical aspects of the product.

Account Manager (AM) [Junior-level]

AMs are closer to a traditional new business sales rep versus a CSM because they typically act as a salesperson than a support person.

They are usually tasked with renewal and upsell quotas from an existing book of customers and focus on the business end of the relationship to win a new year renewal sale.

Why Should You Consider a SaaS Sales Career?

10 Positive Reasons Why You Should Consider SaaS Sales Career

1. Low Barrier to Entry

You don’t need any college degree to do sales. Yes. Companies or recruiters demand a college degree, but almost 90% of all college degrees are render useless in sales (actual individual contributor, taking to prospects and getting results type of sales). The skill is not hard to learn or master.

Especially the SDR role. There is no prerequisite to do this role and exceed. What it takes is strong willpower, discipline, consistency, courage to do cold outreach, and the hunger to succeed. That’s why most new grads or career changers happen upon sales.

Also, there’s no right type of person who can succeed in sales. Why? Regardless of your profession, everyone is engaged in sales even if that’s not your full-time, 9-5 gig. I know introverts who smoke extroverts in smashing their quota, etc.

2. Potentially Lucrative

In software sales, you can make 6 figures or more if you hit or exceed your quota. Piggybacking from point (1), it’s a more compelling career option if you hate studying or do not want to go back to school.

And for individuals who stay in this field and move into enterprise sales, you can make up to half a million $$$ and more. There is potentially no limit to how much money you make and you don’t have a salary cap on commissions you earn.

3. Build Solid Business Acumen

If you ever dream to be an entrepreneur or a CEO of a company or to run your own business, having Sales background, experience, and training will go a long way for you.

In Sales, you will learn how to prospect for new leads, understand how to qualify an opportunity, negotiation, and persuade people to buy your solution for actual $$$.

I’ve seen SDRs or other salespersons on LinkedIn who started their own company with a technical co-founder. Being in a sales role is like a condensed, affordable, more practical MBA education than a traditional MBA.

4. Career Mobility and Progression

You do well in sales, hit your numbers, and blow out your quota. You will be recognized in the company as the breadwinner. With that merit, you can leverage that to earn management roles or more lucrative sales roles selling into bigger enterprise accounts.

Or starting from an SDR, you can transition to Marketing, Customer Success, Management, or in rare cases into Product if you have suffice technical skill set acquired during your tenure at a given company.

5. Visibility of an Entire Business

You will have more exposure to the entire org than other roles because you will interface with Marketing, Customer Success, Support, Product, Engineering, and the Executive team.

Hence, you will develop a holistic view of the business you are in from both the internal company facing side and external customer facing side.

6. Self-Autonomy

If you are hitting your numbers and your boss is cool, you can work from home or remotely, get off earlier from work, etc.

Granted, this is a double edged sword. If you are missing quota and not hitting your numbers. You will be micromanaged.

But for the most part, salesperson have the greatest autonomy in a company next to software engineers.

7. People Oriented Work

If you are an extrovert and engage talking to people. That’s what you will be doing in sales (in an AE or full cycle sales SDR role).

You will outsource and delegate other things like Marketing collateral, Sales Enablement tools, Sales Operation tasks, and Technical Support work to other team members and focus on talking to prospects and selling.  

8. Understand The Real Market Pain Points & Problems

This is where individuals who want to engage in entrepreneurship really can benefit. You have front row seats in interacting with prospective customers who are experiencing a specific pain in the market, and you have the opportunity to qualify and scope out that problem and potentially leverage your company’s product as a potential solution.

This process, experience, and knowledge is colossal if you were to ever do your own start-up because you will understand what really is important to a business: driving sales by having prospects actually pay money for your product.

9. Sales is a Universal Skill That Helps You Anywhere

Developing a strong sales skills will improve and benefit other aspects of your life whether professional or personal.

The fact is, everyone is a salesperson, just to varying degrees of success and effectiveness. Sales will teach you how to communicate (both passive and active aspects of communication), negotiate, and handle subjective, objective situations by employing reason and emotions to problem solving.

10. Perks and Incentives

For high performers, incentives and perks are not just monetary. You might have stronger influence in the company because your word, advise directly impacts the financial success of the company.

For other perks, in bigger companies, there are competitions for cash prizes, vacations, etc for the top salesperson who rakes in the big $$$.

And as we already mentioned, autonomy is a big perk.

10 Negative Reasons Why You Should NOT Consider SaaS Sales Career

1. Easy Come Easy Go (High turnovers)

Sales is a black and white, cut-throat type of profession. Turnovers can happen when a salesperson fails to perform, the market changes the demand of the product, company politics, bad bosses, toxic sales org culture and other reasons.

The average turnover rate for sales org is 34% of both voluntary and involuntary. Meaning that out of 4 hires, 1 person either got fired or let go, and another person might be in-danger of the same fate.

Research from SiriusDecisions shows these stats:

  • 89% leave due to deficient compensation.
  • 60%-80% leave due to lack of connection with leadership or incompetence of leadership.
  • 75% leave because of concerns about the company ability to meet market needs.

2. High Reward Comes With High Stress: #burnouts

Stress comes from dealing with external factors like unpredictable, uncontrollable prospects who have their own agenda and don’t care if you need to hit your sales quota and internal factors like competition with colleagues; a demanding, unreasonable boss; and leadership team creating unrealistic sales targets.

The role itself is stressful also, especially if you are doing outbound sales as an SDR because you will face daily rejection and lots of uncertainties.

That huge amount of stress leads to a lot of salesperson burnouts, I’ve personally experienced this for myself where there will be weeks where I will push 10-12 hour days meeting with clients and trying to close business before a quarter ends.

3. Work is Mundane, Repetitive

This holds especially true for telemarking SDR roles where it is just “smile and dial” type of function.

You don’t really learn anything more than busting cold calls and preserving through rejections other than grit.

While grit is important, but its not efficient or effective long term versus other professions, like Product Management, Marketing, Engineering, where if you build your skills there long enough, you can automate repetitive tasks and focus on higher level activities that require more brainpower.

Granted, higher-senior-level sales roles, like being an Enterprise AE is a more engaging fun role. But the competition and cost of acquiring a position like this is difficult and an uphill battle.

4. Stuck in Sales Related Career Path

In this day and age, people change careers or jobs 10 to 15 times throughout their lifetime. But with a sales background, it’s hard to move out of this perpetual grind career path.

Why? Because salespeople (normally, the majority) lack a technical or niche hard skill like coding, accounting, or some sort of specialized skill.

Granted, you can always argue that sales itself is a hard skill, and I would agree, if you specialized in a specific vertical (i.e. HR Tech, health, energy, etc); then you will be armed with industry specific knowledge plus the skill of selling to that specific niche.

Nevertheless, sales, in general, is a broad skillset. If you wanted to switch into another career that’s more specialized to some degree (digital marketing: content, product, growth marketing or some technical role: business analyst, operations, etc), then you will get weeded out because it requires specific, specialized skills to be qualified.

hereas, sales in large has broad qualifications making it easier for people to enter this career.

5. You Are A Clog in an Endless, Perpetual Machine

A VP of Sales told me once what they expect in their sales reps: “Your boss just cares that you do your role, hit your numbers, and don’t cause trouble. It’s like a cog in a machine.”

Do you want to be just a cog in a machine? Even if you are the highest performing salesperson, the company executives will still view you as a cog in their machine and get rid of you for the sake of the company.

Yes. There is that pride of being a good salesperson when you are overachieving and doing well for a company, but again, you are a replaceable cog.

6. Lack of Real Collaboration That’s Not Competitive

In sales, there lacks true collaboration towards a common goal. You can argue that hitting company quota is a collective, common goal. Fine. I give you that.

But in the day-to-day life of a salesperson, you are effectively your own CEO of our island (territory).

Your colleagues are competitors who, if they do better than you and exceed their quota, will be up in line for promotions and other perks.

What’s more, there is no incentive for your colleagues to help you succeed. Their success is directly tied to achieving and exceeding their quota.

7. Customer Facing Role Pains: People hate salespersons

I hate sales people. Period. I like Sales and understand the importance of it. But I hate sales people.

Whenever my phone rings from an unknown number, I am already on the defensive of expecting a telemarketer trying to sell me something.

Your prospects are human, no different from you, they also hate sales people.

8. Success is Not Always Directly Correlated to Your Hard Work

Chance. Luck. Being at the right place, right time, right person, right words, right pitch, right opportunity.

Those probabilities are hard to get all of them lined up. But in Sales, that’s how it works. You find qualified buyers by slamming your head against a phone or spraying email campaigns to your prospect list to weed out unqualified buyers.

Think of how you buy something. You already wanted to buy that thing because you had a need. Not everyone you reach out to will have that need.

Therefore, purely hustling and throwing hard work sometimes isn’t the right solutions. I get it. Sales is a numbers game, but number games are rigged for failure if the probability of success is close to 0.

Sometimes, your lack of performance as salesperson is not your fault. But in the eyes of your boss and company, it is. And that’s frustrating.

9. Lack of a Solid, Hard Skill

Sales like I mentioned is a skill everyone uses. It’s categorized as a soft skill. It’s not difficult to pick up or master. Thus, the competition is steep because everyone can be qualified to do sales.

Yes. Sales is hard. But not due to the nature of the skill itself, but based on the circumstances in which you have to play your skills correctly.

In other fields like software development for example, it’s quite black and white what success looks like because there is a normally a yes or no answer or solution to a given problem.

You can actually solve a problem if it’s possible to solve it by employing the right solutions and tools.

In Sales, the number aspect of it is very black and white, but the outcomes are a stupid, weird color of gray.

For the sole reason that hard work doesn’t directly mean you will be successful in your outcome (if success was framed in monetary gains, etc).

10. The Grind is 24/7

The rat race is never done. At the beginning of each new day, week, month, quarter, and year; your target numbers will refresh and you will wonder the point of your existence and ponder at the profound number of starting from 0 again.

Admittedly, if you do well in Sales, the constant thing that should not change is your increased, fast accumulation of cash.

But again, is that enough to justify the perpetual grind for you? Close to recruiting but just a little different, you have to be on all the time for clients who might want to buy.

Work-life balance can be an issue because it becomes work-life integration. That might be a deal breaker for people. Maybe not for a short-term session, but considering this career path as a long-term.

Now that  I’ve outlined the pros and cons, and you are still interested. We can talk about how you can start your sales career.

How Can You Get Started With Your SaaS Sales Career?

I would leverage recruiters to help place you into companies and sales bootcamps to help train you (and place you) in basic sales methodologies, etc.

Vendition – Sales Bootcamp

I was the 42nd candidate of this program. They give you a 1 week online training and then place you into companies within the span of 3 months in what they call a “sales apprenticeship” where you have a sales mentor to guide you through your first sales gig.

Always Hired

I’ve had co-workers who came out of this sales bootcamp/recruiting agency and they seem to be doing well.

Sales Recruiting Agencies (San Francisco Bay Area)

  1. Betts Recruiting: This agency is super picky with candidates and will only place you if you have a clean state or a strong track record.
  2. TheLions: I’ve been placed into a company with this agency. I recommend them. They actually work with you hand to hand to prep you throughout the entire interview process.
  3. Rainmakers: A different recruiting model where employers fight to hire you. This is a great option if you are an exceptional performer, but if you are just getting started, you should try TheLions, AlwaysHired, or Vendition.

My Advice If You Wish to Proceed with Software Sales

If you are fixed on trying to give software sales a chance, do your best to find a full sales cycle role (SMB AE or full sales cycle SDR) if you are a fresh college grad or you are switching from another career, do your best to land an SMB AE or full sales cycle role also.

Here are the reasons why:

(1) Closing Experience: This means getting the chase to close deals and actually making $$$ sales. Sales recruiters who wish to fill AE or closing roles want to see that you have at least 6 months or preferably 1 year closing experience for most other AE roles on the small business side.

Therefore, the faster you can accumulate this experience, regardless of the deal size, the better because you can always make an argument for why you would be competent for a larger deal size type of closing role based on demonstrating your business acumen.

(2) Business Acumen: Since a full cycle sales role encompasses the entire sales process from prospecting leads to closing them, you will experience the full spectrum of sales and learn about the nuances of getting a lead pass each sales stages and the challenges involved.

Smarter, more skillful salespersons will develop scalable, repeatable processes to help them identify and qualify leads into sales opportunities faster.

This ability to create a scalable sales process to qualify opportunities is a very transferable skill amongst sales roles because it’s the very foundation of the perpetual sales engine.

The only difference is that the sales process will differ based on which market you are targeting (small, mid-market, or enterprise)

(3) Learn More: In conjunction with point (2), you will learn way more in a full cycle sales role than a regular SDR or a closing AE role because you are in charge of the entire new business side of sales.

You will have to learn how to prospect leads, generate leads, qualify leads (multiple times during each sales meeting based on their sales stage), handle objections in each of these sales stages, negotiate terms and prices, and close the actual deal.

(4) It’s More Fun & Rewarding: As a regular SDR, your sole purpose is to prospect, qualify and pass leads to AEs. That’s betting on whether its a decent SDR role. Most SDR roles are smile and dial, get a lead interested enough to take a meeting with someone else.

In a full sales cycle role, you are responsible for everything. Yes, this is more stressful, challenging, and more work; but its worth every bit of it because you will learn a lot more.

I argue that it’s more fun and rewarding because you are actually impacting the company you are serving by generating revenue.

Not just your company, but you are serving your clients better because they have 1 point of contact in the sales cycle versus talking to potentially 2 or more salespersons in the process.

This will give you more insight into your client’s challenges and pain points in which you can devise helpful solutions in each sales meeting up to them buying from you.

In summary, by getting a full sales cycle role, you will learn more and actually develop your sales skills, get closing experience under your belt so that you can shoot for higher paying AE roles at bigger companies that targets mid-market, enterprise accounts.

Sales Career Alternatives: Digital Marketing

This is an umbrella term because digital marketing is vast. I would recommend trying a digital marketing course by Engineered Truth and Seth Jared.

There’s other facets like content marketing (writing blog content), affiliate marketing (brand partnerships), and video marketing (YouTube, etc).

These alternatives are harder to start and are not lucrative right off the bat, but they can grow into something rewarding and lucrative.

I personally wish I started doing digital marketing: content creation via blog, video, etc sooner.

Had I a chance to do it over, I would probably do a CSA role because its more stable, transfer into marketing and in my spare time, build my digital marketing skills and digital brand presence.

Sales Career Alternatives: Software Development

This is has been a long time coming for me since 2017 when the thought of becoming a software developer resurfaced.

During my university years, to be transparent, I was afraid of computer sciencing and coding. I didn’t believe myself to be smart enough.

Fast forward to the present me, who went through various resources like freeCodeCamp, Udemy software development courses, and fun, inspiring conversations with other developers; I’ve found the courage to give this career path an opportunity because I think it might be a good fit for me.

In the future, I will post my experience with this online 3-month full stack Javascript coding boot camp I am considering to attend from January to April 2019 called Bloc.io where I will attend the Web Developer Track over this other boot camp called Covalence.

This path definitely will be the harder of the 2 other mentioned path, but it’s a great skillset to possess for the future that will be more and more technically oriented.

I will post frequent content about my bootcamp experience and outcomes in the next 6-9 months.

Stay tuned for that and subscribe to my newsletter if you want to go through the journey with me.

Was This Helpful? Please Support 🙂

I hope that this blog can challenge your thoughts on considering whether a career in software sales is a good fit for you as a recent college grad or career changer.

I would love your support by clicking into these Amazon affiliate links in my tools page and go through your normal purchasing habits. Or you can join my Patreon community.

Doing this will support this blog and my other resources like my YouTube channel so I can continue to produce high quality, useful content on a weekly basis.

This blog was made to serve you. Enjoy.

This blog has been inspired by these creators: Dan Lok, Roberto Blake, Engineered Truth, Seth Jared.


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