Below is an excerpt from the Career Options chapter of a book I'm writing loosely titled
"They Call It The Real World: Mastering Your 20’s in the 2010’s"
A Guide to Thriving Personally and Professionally During the Best 10 Years of Your Life
(Publishers and literary agents, let's talk.)
Everything a college junior needs to know before embarking on a career in sales....
Entry-level sales tends to be a catch-all for likeable, energetic and money-motivated graduates who haven’t yet specialized in a particular skill set or industry. Since few parents encourage their children to pursue the inherently unstable world of sales in place of more steady professions like law or accounting, and since few colleges offer anything beyond the most surface level classroom explorations of sales best practices, the workforce of the sales economy is largely fueled by early career vagabonds seeking a respectable title and compelling financial upside. Often a sales interview is where people end up when they’re just looking for ‘a job’ because nothing else seemed interesting or appropriate, and that’s OK.
Most new grads gravitate towards outside sales, preferring the freedom of face-to-face contact over the heavily monitored phone and email solicitation of with inside sales. Many roles are hybrids though, with the majority of legwork work done remotely followed by physical meetings as needed. Cutting out the majority of travel allows for greater economy of scale hitting on more prospects in a given day, particularly in high volume sales organizations where presumably smaller deals requiring less intimacy are entrusted to the new blood. It’s also hard to mentor a scattered sales force, so frustrated outside sales newbies often find themselves craving a more structured environment after a few months on their own fleeing security guards and getting literal doors slammed in their literal faces by literal gatekeepers. My suggestion is to pursue a role where most of the work is remote, with occasional field trips to meetings and trade shows mixed in, curbing the office monotony. This recommendation probably puts you in the ‘appointment setter’ role initially, at least for more enterprise-level sales programs, which is fine. You can learn from more seasoned sales pros while watching them close deals and earn you both a commission.
Hustlers, jokers, studs and princesses, it’s time to capitalize on the charm that’s helped you skate through situations where less captivating characters get tripped. While sales experts correctly stress that achieving sales success is more about technique, attitude and process than the squishier concept of having-sharp tongued people skills, social confidence is still a core building block on the path to sales greatness. Lovably clueless jocks and divas, a career in sales is the best way to harness your natural magnetism. Goofballs, even annoying ones, there’s room for you too, as you tend to thrive when people only meet you in small doses. Entrepreneurial types score favorably in sales aptitude as well, because they inherently accept that fluctuating pay is a necessary obstacle on the path to big paydays.
Success and failure are both public information in sales. It takes resiliently thick skin, but really just about anyone with a positive inclination, high risk tolerance and steadfast work ethic can find their niche. Being good looking helps too…oddly, even over the phone.
Who Doesn’t Belong:
Whiners, downers, sloths and anybody else with a self-righteous air of entitlement. Fundamentally, sales is about listening to other people’s problems and presenting solutions, so those too caught up in their own plight or opinions need not apply. Many know-it-alls who fancy themselves to be charismatic leaders get their first dose of humility failing early at sales, finding that clients are looking for a consultation, not a lecture. Regardless of industry, and especially in the early goings of establishing a book of business, your compensation will be directly tied to your output of effort, so you need the mental toughness to continue plodding towards goals in the face of near-constant rejection. Organization is profoundly important too for prioritizing a sales pipeline and executing orders, so frequently late and lost scatterbrains tend to get fired quickly after repeated bungles do serious damage to a company’s operations. You can’t be too rigid though, because uncertainty comes in waves when deals go bad and quota deadlines loom. The key is a preference for managing chaos rather than avoiding or causing it.
What to look for:
Unless you’re willing to deal with the pay and lifestyle instability that comes with a startup, look for a growing company with at least somewhat of an established reputation in an industry you actually find intriguing. The interview should be one-one-one, not a cattle-call, and the job should come with a barely livable base that allows you to pay your rent while ramping up a book of business. The base may in fact be a ‘draw’ in industries like real estate and ad sales, meaning it needs to be paid back from future commissions, but that’s fine so long as you at least get health benefits. Training should extend beyond a few days of boot-camp style company indoctrination, with regularly scheduled meetings to review your performance with a direct manager who can help you find your legs. Activity metrics and process documentation procedures should be clearly laid out, explaining in detail what best practices are expected from new hires for them to meet expectations and how this impacts their income potential.
They should be investing in you. Grooming you. Giving you every chance to grow with the company so long as you stick with the program. Churn, a term referring to the frequency of employee turnover, should be low. Everyone lies about churn, and sales managers are the biggest offenders, making it seem like the only people who don’t make six figures within two years are lazy wretches, so run from anybody who admits they lose over half the sales force within a year.
Leads should not be confused with lists. A sales lead is somebody who has actively indicated an interest in purchasing your product. A list is what’s handed to you just before being told to piss off. Whenever possible, choose a sales job where recently submitted and verified leads are provided for you to pursue the business. These may be the small potatoes handed down from rainmakers too busy for the scraps, or they may be collected through your company website or a marketing partner. Regardless, you’ll most likely be in charge of qualifying lukewarm leads and then passing them along to be closed by somebody else once hot. This is entirely better than cold calling a phone book or office complex, and the best sales jobs let you learn slowly with a team instead of throwing you to the wolves running the whole process solo from start to close.
What to avoid:
The bottom rung of sales careers goes by many names - Multi-Level-Marketing, Pay-to-Play, Pyramid Schemes, even Entrepreneurship. Usually it starts with posting your resume on a site like Monster or Career Builder, followed by a call from an enthusiastic recruiter at an impressively named financial services (really, life insurance), telecom, health and beauty supply, medical device or office products company. On interview day, they’ll bring you and the rest of today’s ragtag crew into a conference room, parading a few spit-fire high earners to the front so they can charismatically weave their inspiring rags-to-riches stories between a few vaguely informative slides. Next, whether you’re interested in selling their wares or not, they’ll ask you for a list of your family and friends along with their contact information so they can “reach out on your behalf”. Some will even ask you to pay a ‘franchise’ or ‘membership’ fee, buying the right to build your own business by hiring a harem of young bucks under you and earn ever-growing piles of commission the same way they did. It can be a cult-like experience, making you intensely want to join and run away at alternating moments. Choose the latter.
Sales is a sink-or-swim profession, making high turnover a surety. Churn (a term referring to the frequency of employee washouts) however, should still be lower than a year on average, meaning most new hires make it through the first 12 months before quitting or being shown the door. Everyone lies about churn, and sales managers are the biggest offenders, making it seem like the only people who don’t make six figures within two years are lazy wretches. Run from anybody who admits they lose over half their sales force within a year.
Large companies tend to make larger sales, and the interview process will be accordingly complex, often with multiple tiers of rapid-fire group interviews, informal personal conversations and mock sales appointments. Study the company hard, and don’t be afraid to disagree when challenged. They want to see if you can hang tough through the ups and downs of a convoluted sales cycle.
Small companies and higher volume sales tend to be more straight-forward in recruiting new hires, looking for “fearless hunters” capable of knocking down doors come hell or tsunami. This sale is less strategic and more dogged. Unshakable confidence and a sunny surface-level disposition will get you an offer. It’s just on you to keep up the show for the offer to be worth anything.
Appearance, tone and attitude can get you in the door of just about any sales organization hiring entry-level talent. Eye contact and an assertive hand shake are a good start too. Separate yourself from the pack by asking questions about competitive differentiation, daily performance expectations and the future of the industry. Don’t be afraid to dig deep into the compensation package, being sure to uncover any hidden trap doors either capping or negating commissions. After all, you’re going into the business of talking about and asking people for money.
“You get out what you put in. The sky is the limit” – Heard every first day on the job as a sales newbie.
Look, you weren’t hired out of college for your industry connections and experience. They brought you in because you still have the eager vigor necessary to endure the grinding monotony taking place at the start of a sales cycle. Performance is rewarded above all else, and it’s not necessarily tied to effort. Luck is often the key to success, but you’ve got to put yourself in the right place to get lucky by executing constantly, as luck rarely comes to those who wait.
There’s really no such thing as being off the clock either. You can always do more research, make more phone calls and send another email. Being the first to reach a prospect or reply to their inquiry is often the difference between a sale and a tough conversation about an ‘improvement plan’ with your manager and an HR rep. This means blurring the line between your personal and professional life, taking calls and prioritizing activities at all hours.
Privacy has little place in sales. Discretion with clients certainly does, but internally your performance will be highly visible to peers, creating a healthy competition for bonuses and promotions. If the job is worth having, all customer and prospect interactions will be recorded in an online Customer Relationship Management system (CRM), accessible to varying levels of employees. A popular adage is “if it isn’t documented, you didn’t do it”, because your manager is largely paid to keep you on pace with projections, and they need this insight on demand, so make sure your trail sparkles with the right activity. If you’re following a process that’s been successful, the logic goes that a good hire will succeed with minimal mentoring all outside variables remaining equal.
Your product is the star of the show. Unfortunately, most sales training programs are more about company indoctrination and process reinforcement than actually learning about what you’re selling and why it’s special compared with anything else on the market. Your first week will look something like: Day 1 – Welcome speech from top dog followed by brutal payroll and healthcare paperwork. Day 2 – Obligatory motivational speech by washed up sales manager followed by a sobering review of periodic and revenue production expectations. Day 3 – Product Review. Day 4 – Process review. Day 5 – Role playing. That’s it. Then you’re thrown to the wolves so you can fall on your face, and occasionally a manager will ride along or sit on a call to tell you what you did wrong.
Two important elements typically left out are the nitty-gritty of competitive differentiation and setting up ongoing mentoring opportunities to learn alongside those who have weathered the storm, finding ways to close business in good times and bad. These aspects of training are often omitted for good reason. The competition is constantly changing to better compete, and nothing stymies the enthusiasm of a new hire like learning their new employer is hiding how tough it will be to outsell the competition in a crowded market with super-informed customers. Take it upon yourself to supplement the cheerleading, basic offering summaries and procedural expectations set out in formal training by becoming a student of your industry and actively seeking opportunities for real-time exposure to the sales process of top earners. Constantly evolve your industry competency and sales technique. Dedicate an hour every day to reading sales and industry blogs, newsletters and discussion forums, and stroke the healthy egos of rainmakers by offering to buy them lunch (which they’ll end up paying for) if you can accompany them visiting clients or calling top prospects. You’ll become an expert, adding to your credibility and attractiveness as a future job candidate in the field, and you’ll be exposed to what actually happens at the top of the sales funnel.
At best, base pay will be about half your yearly on target earnings (OTE), meaning you’ve got to produce new business to get paid, and you’d be hard pressed to lock in a salary beyond $30k. You may have to settle for an equivalent IOU, or ‘draw’, to get by in the short term until sales kick in. Again, commission-only gigs mean the company isn’t investing in you, and I strongly urge you to avoid them. Embarking on a career in sales means you need to constantly close deals in order to earn a respectable living. This is great motivation for staying productive while salary-only friends enjoy their income-capped time off, but it’s also demoralizing when these same friends spend with confidence as you turn down plans to go out because failing to hit quota cost you this month’s beer money. Be patiently consistent and headstrong paying your dues. You’ll out-earn everybody in a couple years.
Part of proper sales execution is creating the mystique of success. This means presenting yourself as financially comfortable and personally confident at all times. Outside sales pros will be required to dress to impress, because nobody wants to buy from a slob. The level of formality varies by industry, but you’ll generally need to be at least equal in apparel to your target customer, if not one step more fashionable. Inside sales tends to be more of a free-for-all, sometimes allowing t-shirts and sandals in the name of a cool corporate culture, which really means the brass can’t justify being hard-asses on attire when asking twenty-somethings to sit in cubicles for long hours grinding out phone calls.
Sports analogies appropriately abound (Manager = Coach. CEO = GM. Sales Rep/Sales Associate/Account Executive = Player.), and the locker room of a sales organization is a cliquey place with veterans and all-stars garnering the majority of attention and influence. In the end, nothing speaks louder than the undeniable power of bringing in business, but advantages like the hottest leads and prime territories tend to be granted to those who get on the brass’s good side. Mistakes and poor results get glossed over for the cool kids, but haunt those out of social favor relentlessly until the numbers speak for themselves, upon which time recent top earners suddenly get an invite to the off-night card game.
Be warned, the underpaid peons actually servicing your orders in other facets of the company will grow to resent your success. They see the sales department as a bunch of lazy idiots profiting without merit while everyone else scrapes by. Pay this no mind. Sales jobs are easy to get, and they are free to apply if they’re willing to sacrifice safety for the pressure of producing revenue by asking people for money. Just make sure you thank everyone helping you, because they’re the people you’ll need favors from getting the dirty work done closing deals with a looming deadline, and the last thing you want is your own reputation and organization working against you. A little goes a long way letting everyone know you appreciate their help.
Sales contests are a peach. Play number one in the ‘How to Juice Sales’ playbook is to dangle a highly desirable prize as a bonus for the highest producer of whatever metric needs improvement in a given time period. It may be a vacation, gadget or gift card. Whatever, it’s basically free money for doing what you’re paid to do, which is make everyone - including yourself – a pile of cash. Sales pros are incentivized to produce of all else. Enjoy.
Job security is flinty in sales. Income stability too. Failures tend to be gruesomely public displays of inadequacy, especially in shops where the scoreboard is kept public for all to see. Cutting the dead weight in the bottom tier of producers and replacing them with a fresh new crop of doe-eyed sales guns simply makes good business sense. The good news is you usually know when the end is coming, which provides the opportunity to hustle for a turnaround or seek new opportunities before the door hits you on the way out. It’s all very much “What have you done for me lately?”
Personal time and freedom are an interesting give-and-take in sales. One on hand, you’re an independent business owner left to define how you spend your time so long as the results speak for themselves. On the other, customers and prospects demand that you be available at their whim, lest they take their business elsewhere, getting more attention from the competitor pining for their attention with promises of 24/7/365 availability. For those incapable of handling a lack of 9-5 structure, the freedom to self-manage can be a burden. Conversely, those who need their personal time to stay that way unquestionably may struggle with the burden of an on-demand industry.
2 Years Out:
Plenty of people start out in sales. Only a select few survive the first 24 months though, and those who do are faced with a difficult decision of whether to embrace an even higher level of risk pursuing bigger accounts at the same company or a poaching, up-market competitor, or to bask in the shelter of management, delivering the same schlocky rah-rah spiel to newbies you half-heartedly bought into only a short time ago. Leaving sales means giving up big dollars for security. Staying in means the pressure to produce remains at large, or at least the pressure to help others produce does. Your bank account and blood pressure will make the right decision obvious.
5 Years Out:
You’re pushing 30, the grind has eased, and the time has come for defining your career path long-term. On one hand, you’ve had a good run making a solid living and having fun. On the other, you don’t own any equity, and your entrepreneurial drive is what attracted you to sales in the first place. Maybe it’s time to put that nest-egg to work, finally realizing your dream of working for yourself doing what you love. Maybe that promotion is around the corner, or your seemingly run-of-the-mill early account just became a marquee client paying you solid commissions and referral business for years to come. You fancy yourself an entrepreneur more than an employee, even if you’re a faithful company ambassador singing the corporate praises all the way to the bank. Without you, the whole region – maybe even the company – would come to a halt. Major impasse.
10 Years Out:
Life is good. Clients adore you. The company compensates you handsomely for the ongoing revenue of your accounts. Everyone who thought you were crazy for taking on the risk of a career in sales ten years ago now asks you for career advice and sends their cousins your way for a favor getting their resume to the top of the pile when hiring. Sure, you’ve got a few over-extended debts from decisions made when money was flush under the false assumption it would last forever, but all will be well so long as you keep up the pace. Can you though? After all, the industry has changed drastically since you came on board a decade ago, and these kids in the new recruiting class are way more technologically savvy and motivated than you are. Some of your contacts at major accounts have been replaced too.
What if the bottom drops out and you have to go back to cold calling? What if you never get to stop cold calling? The phone keeps ringing, and your inbox is perpetually growing faster than you can work. This isn’t the life you want. Or is it? You wouldn’t have it any other way.