Lately I’ve been a little disorganized. No – that’s an understatement. I’ve been an utterly chaotic tornado of inefficiency.

Today I almost went to lunch instead of leading a 12:15 web demonstration. Somehow I never managed to get it on to my calendar, and luckily another attendee emailed me a confirmation with about 5 minutes to spare, right as I was about to hop off for a $5 footlong.

My task list in Salesforce.com is 98% red, meaning OVERDUE, some of them months old. Sure, every time I look at them they don’t strike me as any level of priority… but some sick, sad, inner professional masochist will not allow me to delete them so I can start fresh with my latest tasks.

I’m flying to Houston Wednesday… and I just booked my flight on Saturday. You don’t want to know how much that cost. I still have marketing emails to send out in preparation for that, but somehow they elude me.

I have an enormously important demonstration at 1 PM tomorrow, part of an RFP process and it’s going to follow a 4 page demo script. I just realized it’s happening and looked at the script for the first time at about 3:30 PM today. I died a little on the inside.

I have this fantastic theoretical awareness of how I should be organizing myself, but my To Do lists are still scattered pieces of yellow notebook paper, etched with fierce cross-outs and giant bullet points. Business cards are strewn about, semi-prioritized in mini stacks under and around my keyboard. The amount of scrap paper cluttering my work area (and expanding beyond into 2 more work areas) would make Al Gore weep.

What’s the secret? Is it just me? I’m remarkably OCD about a lot of things. Maybe I’m just overworked and heading towards burnout and getting on top of things is simply impossible right now. I don’t think that’s it though. I’d love to hear some of our readers’ tips for handling work/information/stress overload…

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

Lately I’ve been hitting some snags in my sales cycle. Without a doubt, my strength lies in the early stages of the sale. I have diverse and creative methods for finding leads, including strategic Twitter feeds,  discussion forums, and bartering with partners. As the Marketing Manager for the past two years, I’ve been crafting our messaging, so I know it inside and out and can generate interest very quickly and lock in meetings.

However, I’m having trouble closing. I even watched the Glengarry Glenross monologue a couple times, and while feeling motivated (and a little browbeaten), I don’t feel educated.

I try to reassure myself that my current losses must be chalked up to experience, but that doesn’t satisfy. I’ve closed a few big deals after all – was I just lucky? Perhaps. I think there are very finely honed skills, intuition really, a sense of where the buyer’s head is and what to do next, that I have seen in experienced account executives I’ve worked alongside lately – and I do not have those skills.

I was working a pretty fair sized deal, over the course of about 2 months, and was feeling the pressure to close it by the end of February. Our sales coach gave me some advice during our sales meeting to push for the close and offer up a meeting of “executive sponsors.” I was so amped, I called right after the meeting. I left a message and got an immediate callback – the prospect must’ve been on the phone when I called. I could sense the cold, sharp tone in her voice as soon as the conversation started – and it only got worse. As I carried out my proposition, and explained I was calling to check in and see how realistic a February close was, I was faced with a no-nonsense reply – that I was “pushing too hard” and “it’s not going to happen.” Ouch!

Needless to say, I’ve backed off. But when do I revisit? I had a great offer on the table, and they really are a perfect fit for our services. Did I kill it? I feel like the honeymoon’s over, and I’m faced with a totally different situation. Similar to the Ben Stiller remake of “The Heartbreak Kid” – but possibly less painful an experience.

Another case, even more brutal because I’m pretty sure we didn’t do anything wrong. The largest deal I’ve ever been a part of has been a 4-month long RFP process, of which we made it from 10 vendors, down to the final 3. Then we hear that the project has been axed by the CFO, and that we were chosen as the winning vendor before it happened. Twist the knife, why don’t you!? I know this one seems out of our control, but we have to try, right? I feel frozen in my tracks on this one, just no idea how to proceed without appearing to disregard an executive decision.  At the same time I feel I’m trying to change minds, even though now my interests feel too selfishly motivated. It’s easier to have a sense of neutral altruism when you are still trying to win the hearts and minds, as opposed to the dollars and cents.

I found out that I’m losing another deal today because our pricing is more than double what the buyer can justify paying for the service. Ouch again – I am still not entirely comfortable with the part of the sales cycle when you discuss budgets. For open-ended projects that involve high-volume licensing, consulting hours, and in-depth scoping, how do you go about discovering what someone can pay before quoting an astronomical amount? We can’t come back and say, “Oh, just kidding, now that we know you can pay us 40% of our quote, now that’s the price” because it strips all of the meaning from our prices. Is this deal lost, or is this just an opportunity to attempt a negotiation?

Man, closing is tough. I might be unbelievably unlucky and trying to succeed in enterprise sales during the worst economic crisis of my adult lifetime, and maybe it’s good experience getting these hard knocks out of the way early, but I’ll be damned if I don’t go down without a fight on these!

Any sage advice from Daily Anchor readers will go directly towards my selling strategies this month, and I’ll certainly update this thread with my successes and failures. Stay tuned!

Photo credit: Thomas Hawk

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

I recently committed a bit of a networking faux pas, and I will, of course, share the embarrassing details with you in the spirit of opening up some discussion around the topic!

As an avid user of Web 2.0 tools in my social and professional spheres, there’s bound to be some spillover, right? I use Facebook as the primary means to connect with family and friends, LinkedIn to forge professional relationships, and Twitter to scour the web for potential business opportunities, industry news, and even job candidates. However, I’ve got a company page in Facebook, several friends from high school in LinkedIn, and complete strangers in Twitter. And LinkedIn. And, oddly enough, a few total strangers in Facebook, too. So how distinct are these networks, anyway?

I think there may be a line, though, and it is a little blurred – because I definitely crossed it.

As you well know by now, I am an avid Salesforce.com user, advocate and consultant. So I was on Facebook, and ran a general keyword search to see if there were any Salesforce-related Groups, Pages or contacts there that I could interact with. I found tons! Just about every local User Group had a Facebook Group to correspond, as well as Groups for Salesforce.com employees, consulting partners, etc. Naturally, I’d rather be connected than disconnected (“If you’re not first you’re last” -Ricky Bobby), so I started submitting requests to join relevant Groups.

Getting in touch with both customers and employees of Salesforce.com is one of the single most crucial aspects of my job right now, so I browsed through members of the groups. A good percentage I recognized as acquaintances, people I’ve had phone conversations with or met briefly at trade shows and small events. However, a few of them were individuals who I had met with and worked with on a fairly regular basis and felt I knew pretty well.

Throwing caution to the wind, I clicked “Add as Friend.”

Maybe this can only be evaluated on a case-by-case basis, because one of the individuals I added accepted my friend request. However, the other rejected the request, and a little while later I received an invitation from him to connect on LinkedIn. He acknowledged in the invite that “this was a more appropriate place for us to network.” I think he was totally right, and really gracious in his response. It didn’t completely relieve my humiliation and self-loathing – but it helped that he was more of a professional about it than I was.

The interweaving of the social and professional web presents some new territory in etiquette; clearly proven by my intuitive “guilty” response from breaking an unwritten rule. What are the hard and fast rules of networking anyway? Maybe I’m a n00b, or perhaps this is really a gray area for a lot of people. Can you go from mutual following on Twitter to 1st-Tier LinkedIn connection? Should Plaxo be used as a go-between, or can professionals network freely on Facebook, as long as Limited Profile is switched on?

Honestly, I don’t know the answer. I’m pretty sure I was in the wrong here, but I’d like to hear your comments and anecdotes that might shed some light on the subject. It’s OK – I swear I won’t stalk you.

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

DIY or Die? Maybe that’s not the best idea after all.

Last week’s Pro/Con column had me left in the lurch by several colleagues and struggling to complete a lengthy RFP on my own (Read it here.) The shit continued to hit the fan, proving to be one of my largest f-ups to date, so I offer this follow-up.

My assessment that only self-reliance would equal success needs serious re-evaluation. I attempted to complete the RFP with just about a week remaining leading up to the due date, and faced numerous hurdles. My first two read-throughs of the document were not thorough enough, and I overlooked some areas that required time and expertise beyond my capabilities. Having already exhausted several other resources, I was still alone trying to complete it and get it out the door.

I ended up taking some poor advice from a colleague, who had a less-than-flattering impression of the worthiness of the RFP and advised me to put in a corresponding level of effort into my individual responses. I found as more and more of my midnight oil burned, my responses were getting lazier and certainly more terse. A few times I basically refused to respond in detail at this point in the process. This was definitely a mistake.

When I finally rushed the DIY response out the door to our waiting channel partners, the response was not positive – of course I didn’t expect it to be. I was hoping for one of those “it is what it is” moments.

Unfortunately, ambivalence was not the reaction I recieved. Instead, I got reamed for our “amateurish” response, and our overall level of client service was called into question because of my shoddy work product. The incompleteness and last minute response was criticized, and they refused to submit the response to the client, clearly blaming me for their automatic disqualification from the opportunity.

Of course, my instinct is to feel angry about this, and blame others who didn’t support me. I don’t feel that’s very professional of me – and of course I took a very apologetic tone responding to the disgruntled partner. I do take full responsibility. But what is the lesson learned?

Should I have listened to the first colleague, who assessed the situation as one in which we shouldn’t have entered into? It seems so antithetical to me to ever turn down a solid sales opportunity – my economy-embattled marketing dollars went into generating that deal!

Or should I have been a better project manager and delegated, escalating the situation so that resources would have to participate in order to present our organization in the best possible light? This would have required my acknowledgment that it was physically impossible for me to “DIY” – not always easy for my stubborn sense of pride.

Honestly, I’m still left wondering what to take away from the experience. I do know I handled it terribly, but I’m worried if I can’t pinpoint the exact loci of failure, then I’m likely to make the same mistake again.

How does one go about accurately assessing oneself in this type of professional situation? The responses, advice, and criticisms to this mess have been all over the map, and if I can’t determine consensus from myself or my peers, where does the final word come from?

Image credit: mythos arts

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

I’m actually stunned to admit being guilty of this; usually I’m a pretty Do-it-Yourself (DIY) guy. In college, I co-founded a literary magazine in response to the dull school-run rag. At my first job, I initiated and completed a project to go paperless, eliminating two binders worth of unnecessary rainforest byproduct. In my current position, 99% of the time I take the position of “If you want something done right, you’ve got to Do It Yourself!”

It’s that other 1% that really screwed me this time.

I’m sure many of you in Sales can commiserate with me on the pains of RFP responses. For those of you out of the loop, a “Request For Proposal” is a lengthy document distributed to vendors by a company in the market for your product. The vendors respond to detailed questions and requirements by the due date to be considered as a finalist and continue to compete for the business.

This can be unbelievably time consuming for the vendor for little to no return on the investment; it feels a bit like filling out a really complicated Powerball lottery ticket in the business arena.

Typically, I do not work on RFP responses. Now that I’m devoting part of my time to Sales, a certain number of my prospective accounts have associated RFPs. For the past few years, we have had one member of our team who is the designated RFP writer. Naturally, I passed my latest one, (particularly hefty- 124 pages + 50 pages of addendums) to our first responder with about 4 weeks until deadline.

Unfortunately, he sat on it for 2 and a half weeks, and after said period of time, returned it to me with zero percent completed, and informed me that he had no intention of completing it. Awesome!

Having promised our channel partner a timely response, I couldn’t just abandon the project. There were people depending on me! So what did I do? I turned to the next-most qualified individual in the organization to write a response. This person even has a revenue quota that would benefit from participating in the deal. So, scheduling a 2 hour block with him, of course a very busy professional, put our timeline out another week, dangerously close to the deadline.

Upon the first 15 minutes of collaboration, somehow, don’t ask me how, but somehow it was determined that the completion of the RFP was back on me, and the 2 hour meeting was ended before it began.

And now I’m at square one, with 2 days to author a response I’m nowhere close to qualified to complete with accuracy or subject matter expertise. Now I have to rush, work extra hours beyond the workday, and harass colleagues for every additional question I need answers to.

It’s moments like these when I’m reminded why 99% of the time I just do it myself in the first place; not to be pessimistic, but my personal success and reputation is too valuable to place in the hands of people I cannot 100% trust with it.

I’m left wondering if that level of trust can exist; if that is somehow the strongest bond you can have between colleagues and the sign of a great work environment, or if self-interest will always win out in the professional arena?

Your thoughts would be greatly appreciated. My fragile optimism is at stake!

Photo credit: emily august

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

I’m happy to say, I closed my first new account of 2009! Since I’m in a good mood, I thought I’d mix it up a bit this week and analyze the pros and cons of the sales cycle for this win.

Some key stats:

• Turnaround time from lead to close: 23 days (16 business days)
• Number of formal meetings: 1 online, 1 onsite
• Lead source: Channel partner referral
• Relative value: 60% of my Monthly Quota

Pros:

Leveraged partners: As this was a referred by a channel partner, I paid extra attention to key relationships. I became the “project lead,” coordinating the efforts of the channel partner (operating 2,500 mi. from both myself and the prospect) as well as a third partner vendor recommended and demo’ed by me. I maintained control of the communications to the prospect, preventing mixed messages from the multiple parties, and representing a unified front. With all parties completely satisfied by the end, I feel I accomplished this.

Leveraged internal champion: The initial phone conversations and online meetings served as a great way to connect one-on-one with the primary contact, who quickly became a champion and advocate for our solutions. This relationship led to instructive preparation for the on-site visit, suggested by me. The champion wanted the on-site demonstration to go well, and did everything in their power to help me achieve success on that front (despite my nerves.)

On-site visit: This was my first ever solo sales call on-site with a prospect. I was apprehensive and a bit uncomfortable at first, but the key players at the meeting were very down to earth, and I quickly settled into a groove. Though not without hiccups, the on-site visit served to create a sense of “realness” to the often ethereal concept of software-as-a-service. Also, I felt my presence and willingness to meet face to face increased the overall credibility and viability of our organization as a potential “trusted adviser” and solutions provider.

Tireless follow-up: From the moment I heard a verbal cue that I was winning the business, I made closing the deal a top priority. In about a week’s time, I made sure to communicate with the decision-maker each day, as well as continuing coordination with the 3rd parties. Contract negotiation involved calls to their lawyer, nitty-gritty attention to legal detail, and hassling my own CEO/legal counsel for answers. I feel by making it my top priority and not allowing any substantial gaps in activity during the process, I made it impossible for anyone to drop the ball and delay the close.

Cons:

Mastery of technology: I made a huge mistake at the on-site visit by bringing a brand-new laptop…that I had never used before…with Windows Vista on it. This would be the cause of the aforementioned hiccups. It wasn’t entirely the computer’s fault; I only spent about 30 minutes on the machine prepping for the demo. I mostly just tested the projector and opened our application in one browser. I ran into several issues, including delaying the start of the meeting by about 10 minutes because I couldn’t get GoToMeeting to run.

On-site environment prep: It never occurred to me to ask if there was going to be a phone in the meeting room with which to conference in the channel partner. So he ended up on the built-in speaker of one of the prospect’s iPhones, which doesn’t exactly project. As he lost the ability to contribute, I had to pick up the slack and spend more time presenting. I also did a terrible job of preparing for internet connectivity. I failed to bring a network cable, I brought a Sprint wireless card that provided unacceptable bandwidth to demonstrate web apps, and I was incredibly lucky that they had reserved a private wireless network from the hotel where we met. Close call, and SO easily avoided.

Contract preparation: Really, the main reason it took a week to close the deal was my lack of attention to detail on the legalese of our contract. It was mired in inaccuracies that didn’t apply to this type of channel sale, and mostly served to confuse the prospect and their lawyer. This led to several back and forth communications that could have been avoided with some foresight – or at the very least closely reading what I gave someone to sign!

Rookie mistakes…right? I’d love to hear some of your Sales and Marketing horror stories… Please post below!

This column strives to achieve some insight into “best practices” through some of Mike’s own worst practices. Every Tuesday he offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

It all began, as most things do, with good intentions. I had just read fellow contributor Rebecca Novack’s article Smarter Marketing in 2009 for some fresh ideas about fighting the doom and gloom of this economy. I was particularly inspired by the need to focus on current customer satisfaction, retention, and upselling. This is just what I needed in the beginning of the year, as so much of my time is consumed with direct selling; I needed a simple, low-cost campaign to our current client list to boost awareness and motivate the sales team to drive upsells to our most satisfied customers.

At first, I was at a loss for content. I needed something with a clear call to action, that would help us better qualify our customers for add-on revenue potential. Perhaps a survey, or a simple call down the list to check in. In retrospect, this would have been a safe bet.

Brilliant!

I was browsing one of our channel partners’ websites where our applications are listed, and stumbled upon a page announcing “The Best Apps of 2008.” The winners would be determined by the number of 4 and 5-star reviews posted to their listings. This was perfect! Not only would this engage our base, it would increase our viability and outreach to prospects as well.

So I drafted my mass email, polite and humble, thanking our customers for their support and saying that we’d love to hear their success stories because we’re up for an award! I inserted the link for them to post reviews, and my email was sent to several hundred key contacts at our current accounts.

After the email was sent, I also emailed our sales team to inform them of the campaign, as well as the award, so they could advocate for more customer reviews on their individual communications.

Oh Crap…

My seemingly perfect campaign execution hit the skids when I received a call just minutes later from our Director of Client Services, who saw that the email went out. Apparently, there had just been an incident with a client who was fairly disgruntled (there’s always one, right?) and my distribution list included the contacts there. I received an earful about to who, and when, I should send out emails like this.

And I totally deserved it. What could possibly amplify someone’s discontent with a vendor than receiving an email soliciting a 5-star review? I even provided the link to access to the 3rd party site where any comments could be added, and not be moderated by us. This was incredibly stupid of me!

Luckily, the client was not vindictive enough to take the opportunity to bash us, and the email drew an additional four reviews before the award judging. We even won our category!

Lesson Learned

I should never have left it up to chance; if I had put in a couple hours of additional planning, the execution could have been clean, low-risk, and probably have had a higher success rate. Also, my idea of communication was totally backward. I should have alerted the team to the details of my campaign first, and gotten feedback before executing it.

It was undoubtedly a selfish act – I suppose I was thinking if no one else was involved, then I alone deserve credit, right? But upon reflection, credit for the campaign’s success is undeserved and only a product of luck, since it walked such a fine, and unnecessary, line between success and disaster. Failure would’ve been one thing – but marketing campaigns should never carry the risk of hurting the company’s image.

This column strives to achieve some insight into “best practices” through some of Mike Vicchitto’s very own worst practices. Every Tuesday Mike offers up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

This is extremely embarrassing, and unfortunately completely true. However, in the spirit of this column, I must come clean.

Last Friday, I stayed at work beyond 5 PM to help a colleague with some overdue work. My assistance was only required intermittently, so I wanted to use my time productively. I had recently been assigned a new territory, as business had been picking up in the region. We had just brought on 2 clients from New Zealand, and I had a long list of leads to follow up on down under.

I decided to finally set up a Skype account and integrate it with CRM so I could do all this fancy international calling, click-to-dial, auto-call-logging and whatnot. Once I got it all working and started calling, it was so easy and so much fun, I really got into it.

I didn’t have a ton of luck getting any Kiwis on the phone though, and left a dozen or so voicemails. I mentioned this to my colleague who made the astute observation:

“Well yeah, isn’t it Saturday there? What are you doing!?”

Just trying to get ahead?

Ok, bad pun, but I really screwed this one up. I’ve yet to realize any repercussions, but the embarrassment is not going to make the next calls any easier. And it definitely puts a dent in my credibility as their territory’s representative. How could I have not done any research before I got on the phone? It seems so elementary in hindsight. I am usually very diligent in researching my specific prospect before my calls – it never occurred to me to research the territory’s culture, customs or politics (or time zone!) to better prepare me for these calls.

I’ve begun my penance, and have since learned that Australia is also referred to as Oz, the capital is Canberra, NOT Sydney, and their most deadly natural hazard is the heat wave. There are also about 7.5 times more sheep than people in Australia.

Hopefully I can leverage some of this new-found trivia towards rebuilding my international business relationships. I did ask one prospect in New Zealand if he was a fan of Flight of The Conchords (mainly because he sounded EXACTLY like Murray) and it turns out he lived in the same town as Bret and Jemaine!

Now if only I can convince my company that I need to go on location for a walkabout to promote our products…

by Michael Vicchitto | Exclusive to The Daily Anchor

This is the first installment of a weekly column by Daily Anchor Contributing Editor Mike Vicchitto.  This column will strive to achieve some insight into “best practices” through some of Mike’s very own worst practices. Each week Mike will offer up the biggest mistakes, oversights, blunders and bonehead moves he commits in the fast-paced world of software-as-a-service, where he’s a Marketing Manager moonlighting as a Sales Account Executive (at the same company.) Perhaps, in the process, we may learn a thing or two.

…

Today, for starters, I threw away money. This was while I was wearing my Sales hat so it was idiotic on two fronts – I lost out both professionally and personally with this one.

My manager had been working a new account and was ready to seal the deal. He forwarded me an email asking me to draw up the paperwork and close it. My first instinct was to check the account in our CRM and do a little homework. I located the opportunity and saw another Sales rep’s name as the owner of the deal. My logical, ethical Marketing hat took over, and I replied to my manager that the other Sales rep should execute the deal – it’s his account, isn’t it?

It wasn’t.

My silly trust in technology cost me the easiest account I’d ever be able to close. After my boss instructed the other rep to close it out, he let me know he was trying to throw me some low-hanging fruit, that he had been working the deal the whole time and wanted me to close it out and get the win.

I can’t responsibly use the old adage, “don’t look a gift horse in the mouth” to account for this, because I feel my instincts toward fairness and benevolence were right, and I was somewhat bound by duty to act on them.

And then I remember I’m talking about Sales.

The line between Marketing and Sales seems to be fading fast, at least in my world, and I’m going to have to reconcile the two frames of mind if I’m going to succeed in either one. Or both. There’s also the chance I may fail miserably in both realms- at least ensuring a steady stream of content for this column.

Michael Vicchitto is a marketer, sales rep, data management guru, and unofficial Salesforce Consultant. Look for his exclusive article every Tuesday, only at The Daily Anchor.

Photo credit: Ioensis