Dear Bob ... I'm 48 years old with around twenty-five years experience in the industry. I worked my way in and up from night operator. I've been an applications programmer, MIS manager, Tech Support manager and like the rest of us, I've done lots other things in between. My office was recently 'relocated' to the Midwest but all of us chose to stay here in sunny Southern California. ( Dear Bob …I’m 48 years old with around twenty-five years experience in the industry. I worked my way in and up from night operator. I’ve been an applications programmer, MIS manager, Tech Support manager and like the rest of us, I’ve done lots other things in between. My office was recently ‘relocated’ to the Midwest but all of us chose to stay here in sunny Southern California. (Quick side question: If an office is ‘relocated’ but nobody takes the relocation package, isn’t that just another way to avoid saying “layoff?”)I’m seriously considering moving into sales. I know I can be successful so that’s not the issue. The real question is how to get started and make enough money to continue to care for my family and pay my mortgage while I’m learning. I realize I’d be considered a novice even though I’ve been selling informally for years in my different positions. So, what’s the best way to break into Sales without breaking the bank at the same time?– Ready for a changeDear Ready … I’ll answer your quick aside first: No. With a layoff you have no choice – you’re gone. With a relocation, you do. You could have chosen continued employment, along with the atrocious climate, mosquitoes, biting flies and other delights of the Midwest. Instead you decided to go for the great climate, earthquakes, and insane housing costs of southern California.Tough call.Now the advice: It depends. The first decision you have to make is what you want to sell. Selling IT hardware or software is quite different from selling IT services and outsourcing. I’ve watched quite a few people who had been very successful selling hardware and software crash and burn trying to sell IT services.While two of the skills – getting in the door and closing – are the same, most of what happens in between is quite different, including your attitude. With product selling you usually focus on tangibles, such as features, quality, price, or service, that create differentiation from competitors. With IT services you’re more of a consultant and negotiator – the best sales reps in this environment create unique service offerings and deal structures, and call for a lot of insight into the prospect’s business, corporate culture, and personalities, since reaching a close requires consensus among a number of strongly positioned executives.So decide what you want to sell. The other bit depends on how good you are at selling right now, and on your cash reserves. The easiest way I know to break into sales is to offer your services on a pure commission basis. If you can afford to do this, track down a few small companies in your area that probably lack their own sales force and offer to sell for them. Once you’ve made some sales, you can add “Independent marketing representative” to your resume and present a successful track record to the employers you want to work for. I’d recommend against calling sales managers with established sales forces to offer your services on this basis. Their reaction is likely to be, “If the best sales pitch this guy could think of for himself is to offer himself for free, how is he going to succeed selling my company’s stuff?”If you don’t have the cash reserves to go the pure commission route, construct your resume to list your informal selling as real selling (or as close as you can come without being deceitful), read a book or two on strategic selling so you understand the principles, psychology and vocabulary of selling, do the research to identify your key targets – the companies you want to work for – and use the what you’ve learned about selling to sell yourself to the sales managers. The key element of your sales pitch is to list the key skills and process steps needed to sell successfully, and to then demonstrate that you’ve been successful at most of them in past roles. “I will need some coaching on how to cold-call and get in the door, and some help in moving from agreement-in-principle to finalizing the formal contract and deal structure. I’m confident I have the skills to succeed in the rest of the process already.” If you can’t persuade anyone to take you up on whichever of these approaches you choose … maybe you don’t have the aptitude to sell after all.– Bob ——– Technology Industry