IT'S NOT EASY SELLING TO THE C-LEVEL

E-book by: Dailius Wilson

FOREWORD

In sales, we are taught not to count a deal as committable until we have been in contact with the decision maker. What happens if the decision maker isn’t your average, run of the mill manager? What happens when you need the CEO of a large corporation to put pen to paper?

Generally panic.

Don’t worry - as I’ve been there, not only in the past, but many times per week in my current role. It’s not easy. That’s why I’ve written this ebook to help.

During my career, I’ve sold several times to the C-level of Fortune 1000 companies. Until now, these tips and strategies were tribal knowledge; shared with my internal teams or in intimate training seminars.

Now they are all yours!

Unfortunately, I don’t have the time to touch on all the strategies in pages and pages of details - so if you have any questions, feedback, new ideas, or suggestions based on what you’ve read, please send them to my email at drw@getaccept.com

I hope you enjoy this publication so much that you forward it on to your peers and teammates in the sales industry!

Dailius Wilson
VP Sales & Growth
GetAccept

TYPES OF C-LEVEL ROLES AND THEIR PAIN POINTS

Not all C-level decision makers were made equal. Let’s take a look at the main types of executive and what drives them to make key business decisions.

CEO - Chief Executive Officer

The top role in most companies. What many people don’t realize, though, is that CEOs are not all powerful! In public companies, CEOs are answerable to shareholders and in any firm that has raised over $5 million in funding, they are usually answerable to a board of directors. In emerging companies, the CEO can be one of the original founders. In this case, they may hold a higher balance of power than the typical leader.

ONE LINE OF ADVICE

Get to the point quickly and highlight why there would be an ROI for them to personally spend 30 minutes to initially assess the offer; getting delegated to someone on their team is the second best outcome.

PRIORITIES

• Ensuring all departments reach their elected targets for the given year, with the stretch goal of exceeding these results.
• Planning for the next financial year begins immediately as the current year starts.
• Finding and recruiting talented individuals; particularly at the executive level requires a great deal of input.
• Ensuring company culture and employee happiness.
• Reallocating personal time, resources, or talent to address underperforming areas of the business.
• Creating a company vision that will ensure success over common competitors for the next 3-5 years.

PAIN POINTS

• Visibility into the performance of each key department.
• Frustration when delegation doesn’t work; inability to get personally involved.
• Time poor, highly structured day-to-day activities with TOO many meetings.
• Inability to predict future trends with absolute certainty.
• Losing key talent and customers to major competitors.
• Family time and personal health/fitness sacrificed for corporate goals.
• Fundraising efforts if the business is not cash flow positive.

Advice from the pros?

ELAY COHEN

CEO & co-founder, SalesHood
The role of the CEO is to execute the vision and business plan of their company while keeping teams aligned and motivated. Reference their vision and what’s top of mind when reaching out to a CEO. Your outreach and communication should be concise and highly personalized with a specific ask they can easily delegate to one of their leaders.

ROB BROMAGE

Founder & CEO, intelliHR
Today’s CEO must run an agile business, manoeuvring to a ‘guiding north star’ to bring workforces in alignment on mass and engaging them through purpose and inspiration.

They must always be looking into the future, identifying trends, repositioning the business to create new markets that didn’t exist before and, of course, long-term planning. It is also overseeing execution, testing things, adjusting, tinkering, challenging things, speeding things up, slowing things down, and most importantly… calling it… when it is time to pivot.

KRIS RUDEEGRAAP

CEO and Co-Founder, Sendoso
CEOs must focus on people, product, and process in order to build a successful company. People are the foundation and everything starts with hiring, empowering, and engaging the best talent. Great people build great products. Great products will drive results and make customers successful. Once a CEO has built a strong team and found product-market fit, then it’s time to focus on process and scale the business.

CTO - CHIEF TECHNOLOGY OFFICER

The real genius behind the scenes. The positive thing about interacting with a CTO is that features alone can appeal more to this stakeholder than some of the others mentioned in this guide. They’re not always opposed to replacing staff with technology, unlike stakeholders like the CEO or the Chief People Officer.

ONE LINE OF ADVICE

Express a genuine interest in the system/architecture they have built showing T, L, C.
Time saved with your solution, Length of time to implement (shorter the better), Capabilities gained now and in the future for their technical team.

PRIORITIES

• Ensuring 100% uptime of all technical resources.
• Collaborating with product and operations to deploy new technological initiatives.
• Preventing security breaches and monitoring potential vulnerabilities.
• Minimizing unnecessary meetings and focusing on meeting development/IT implementation timelines.
• Researching new technological tools and methods to improve business processes.

PAIN POINTS

• Ever changing technological landscape makes keeping ahead of trends difficult.
• Ensuring the technical team is proficient and up-to-date on all existing technologies.
• Underappreciation from customers and other departments.
• Maintaining high quality control at all times to ensure errors don’t cause business issues.
• Procure funds through a “fear sale” which is a source of irritation. Security risks are ever present; yet many vendors attempt to.

CMO - CHIEF MARKETING OFFICER

The CMO is responsible for the brand, paid lead generation, web presence, key messaging, and marketing materials of an organization. Any good CMO will admit that they are only as good as the sum of their parts; with the marketing organization under them typically extremely loyal and aligned on key goals; typically having worked together at previous companies. The modern CMO can also own the sales development (SDR) function, keeping them well versed in sales tools and methods.

ONE LINE OF ADVICE

CMOs are targeted the most out of any persona so they are extremely hard to reach via phone or email. That being said, they respect quality marketing so if you put effort into the creativity of your approach, you are likely to receive a reply!

PRIORITIES

• Meeting annual targets around lead generation numbers.
• Ensuring a balance of traffic across paid, organic, direct, and referral channels.
• Improving website conversion.
• Staying within 5-10% of the yearly budget.
• Ensuring messaging easily differentiates the brand from other competitors and is being used effectively inside the organization, particularly in sales.
• Approving key design and creative changes.

PAIN POINTS

• Marketing technology can be time-consuming to set up and implement.
• Even if lead generation numbers are high, conversion to revenue is dependent on sales performance; i.e. if sales don’t treat leads well or respond promptly, leads can be fruitless. • Competitor movements or industry change can make brand messaging obsolete quickly; catalyzing constant updates.
• Individual marketing campaigns can be costly so proving ROI (return on investment) quickly can be difficult.

CPO - CHIEF PEOPLE OFFICER

Chief People Officer is an emerging title, with most companies still utilizing the VP of Human Resources or VP, People & Culture. The CPO is in charge of talent acquisition programs, employee happiness, and reducing workplace incidents.

ONE LINE OF ADVICE

HR leaders can be the easiest to bond with, so don’t think the job is done as you successfully build rapport and the conversation is flowing. Budget and technical buy-in can take months to secure, so get these stakeholders involved early.

PRIORITIES

• Reducing employee churn and increasing happiness levels
• Providing a consistent supply of high-quality candidates to all company departments
• Organizing events and programs to promote workplace harmony
• Compliance with local and federal employment legislation
• Creation and promotion of internal company values and policies
• Running a team of internal recruiters effectively

PAIN POINTS

• Recruiting team not hitting their talent acquisition numbers
• Company leaders not respecting cultural or legal practices
• Losing priority candidates to other local firms
• Not receiving a seat at the table in strategic meetings
• Struggle to forge genuine relationships with other employees given HR is the source of all confidential knowledge
• Limited budget, which is often the last to be increased

CRO - CHIEF REVENUE OFFICER

The Chief Revenue Officer is in charge of ensuring sales performance, including new revenue, expansion revenue, renewals, and churn (lost revenue). The CRO may manage the VP of Customer Success and VP of Sales, however, in smaller companies these two functions may operate independently.

ONE LINE OF ADVICE

The CRO, in 9 out of 10 cases, will be from a sales background, so focus on delivering a stellar sales approach in order to secure and further conversations. Remember to include ROI estimates as well as conceptual ideas as the role demands high proficiency with the numbers.

PRIORITIES

• Creation of the sales onboarding and training program for the organization.
• Overachieving quarterly sales targets and reducing customer churn.
• Supervising a technology stack to drive sales effectiveness and efficiency.
• Forecasting and presenting sales trends over the next 12 months.
• Assisting in larger enterprise deals and monitoring the performance of mid-level sales management.
• Decreasing ramp time (the time it takes for salespeople to achieve their quota).

PAIN POINTS

• Forecasting sales results is extremely difficult.
• When the team overperforms sales, targets increase; when the team misses target, often there is no forgiveness.
• Most new hires don’t perform, so increasing stringency of hiring and constant improvements in training are critical.
• Firing underperforming salespeople.
• Not receiving enough “Sales Qualified Leads” from marketing.
• Compensation can often be lower as a CRO than as an individual contributor.
• Managing the egos of salespeople can be taxing.

CFO - CHIEF FINANCIAL OFFICER

If it involves dollar signs, the buck lies with the Chief Financial Officer. In most firms, they are the final signatory on every contract and are in charge of ensuring the company expenditure matches the yearly budget.

ONE LINE OF ADVICE

Don’t mess around - CFOs aren’t fond of small talk and generally want to get down to details, however, if you deliver value you will have business for years to come.

PRIORITIES

• Monitoring company spend across all departments.
• Minimizing unnecessary sources of expenditure including, but not limited to, technology, events, hiring, commission, etc.
• Ensuring that the company’s best interests are covered in all contracts.
• Preparing the company for tax obligations, valuation events, and auditing.

PAIN POINTS

• Reporting expenditure and actual expenditure are often two different numbers.
• Department heads or the CEO may authorize expenditure or amendments to contracts, which are not in the best interests of the company.
• Employee expenses are often lacking detailed information.
• Accounting systems may not integrate with other data sources in the company.
• Leadership doesn’t leave enough margin for error in forecasting.

PREPARING TO MAKE A MOVE

Unlike selling to other stakeholders, where you might be able to rely on chance, timing, raw ability, or a generic approach, selling to the C-level requires you to follow these critical steps before your first outreach.

CAREER HISTORY

LinkedIn is going to be the most helpful resource for this step and the following questions can help you create your note:

• Where did they work before this role? • Did they enjoy success in previous positions i.e. individual performance, company was acquired/ went public etc? • How long have they been in their current tenure? • What did they study initially - does this relate to their current profession?

PERSONAL INTERESTS

Other than reading LinkedIn or Twitter feeds - an unorthodox approach is to contact current or former colleagues with this message:

“Hi $NAME$, I am looking to have a meeting with C-LEVEL-NAME in the next few weeks. I am looking to do an amazing job and I was wondering if you had 1 or 2 points of advice around what I could do to knock it out of the park, maybe any hobbies or interests we’d share in common?”

Watch the results.

SOCIAL ACTIVITY

Monitor what kind of posts your C-level contact is engaging with through likes and comments. Ideally, they are putting out content in written or video form. A great place to look is the company blog as C-levels are often invited to put out 1-2 posts a year or are invited to contribute to industry websites and blogs.

CLOSE CONNECTIONS

Towards the bottom of their LinkedIn profile, you’ll find the recommendations area. This will note colleagues who your chosen C-level has personally endorsed or people who have endorsed their ability. Sort through this list and see if you have anything in common with these individuals (current customer, partner, etc.). If you can’t find anything, see who your second connections are and ask them how well they know the person. A simple introduction could place you one degree of separation away. Worst case scenario, copy the same template from the Personal Interests section above and you may receive a couple of bites!

COMPANY ACTIVITY

Look for news and updates that highlight the company’s current trajectory, recent product launches, customer case studies, and prominent staff hires. Order this by relevancy and recency.

INDUSTRY MOVEMENT

It is your job to ensure you are as well informed about your target industry as possible; you may not know more than the C-level you are targeting, but if they can build respect as an industry authority, you are well on the right track. Try to follow academics and strong publications in the industry on Twitter and use a social media aggregation tool, like Notified, to keep abreast of the latest updates and trends. There is no replacement for reading old-fashioned books too! Try to consume one per month related to your industry.

THE OUTREACH STRATEGY

Once you have completed the research steps above it is time to engage with your C-level contact. Let’s take the following actions:

CRAFT AN EMAIL USING THIS 7 STEP TEMPLATE

SUBJECT LINE: RELATED TO THEIR PERSONAL INTEREST

1st sentence-What you and the C-level share in common 2nd sentence-A comment showcasing what you learnt about them personally 3rd sentence-A question around something in their personal journey 4th sentence-Showcase research which relates to one of the pain points your product solves, ideally with a screenshot 5th sentence-A second question which invites them to elaborate 6th sentence-Describe how what you do solves this pain point and who you do it for 7th sentence-Invite them to contribute some information for you to paint a more accurate picture of how you can solve the pain point

EXAMPLE:

New message

To:

From:

SUBJECT: The most underrated centers in Div II UPenn Basketball

Dear Martin,

Only two centers could understand the pain of having to grab your own rebounds when you are having a bad shooting day - I still play on Monday nights and heard you are still handy around the courts, interested in getting back out there at all?

From my research, I saw you took Salesforce to an IPO from employee 80!

Was it a life-changing experience for your family? What could you see in the company from your earliest memory that made you know it would be successful?

I was able to secure a copy of the proposal your team sent a couple of months ago for the Walmart deal - I noticed it appears tough for your team to personalize the materials in great detail even though the deals are quite high in value.

Would you agree? Have you heard sales leadership bring this up in the office?

We help customers like Samsung, BMW, and 7-Eleven increase the win rate on their proposals through our technology platform.

Could you or the team send me an example of something a bit more recent (with all the confidential details removed) and I can send you back an example of what we could do with it through our platform?

Send

You will notice that my ask isn’t for a meeting or a call. From my sales performance history, I have found that receiving a reply back increases the likelihood of a second response by 200%. Our goal should be to start a conversation and to steer it towards a meeting not to undermine our chances by going for the opportunity too soon.

CONNECT ON LINKEDIN

Add the C-level on LinkedIn - 24 hours later; citing the common interest and a note like this - “Look out for my note in your inbox. From a fellow center.”

STILL NO RESPONSE?

If you receive no response - follow up in two days with the same 7 step template but focus on a different pain point with a new fact you share in common.

REMAIN POLITELY PERSISTANT

Continue to alternate email templates whilst commenting on their personal LinkedIn posts or inviting their opinion on a relevant topic/industry content by using the tagging function.

CREATE A PERSONALIZED VIDEO

Use a technology like GetAccept to present some of your research on the company with screenshots and a personal video - then paste that link and send it to them via LinkedIn. Make sure to paste a logo into the first page of your experience so they see it in the thumbnail and are more likely to click.

TRY A PHONE CALL

After 1-2 weeks of nurture, attempt to elicit a response via phone. If you connect, you will have conducted the research and written enough attempts to have enough material to conduct a meaningful phone conversation.

Remember despite your best efforts selling to the C-level is difficult so you are likely to secure next steps with an average of 2-3% of the contacts you engage. If your results are higher than this you are well on the right track!

SUMMARY OF THE OUTREACH STRATEGY

Craft an email using a 7 step template
Connect on LinkedIn
Still no response?
Remain Politely Persistent
Create a Personalized Video
Try a phone call

YOU’RE GOING TO GET DELEGATED, BUT DON’T PANIC!

Pending your outreach goes well, it will be extremely difficult to keep the C-level contact in further conversations as they are most likely to delegate to someone else in their team. To avoid delegation, try some of these strategies:

• Invite a senior member of your team to participate in the initial call and let the C-level know who is coming to the conversation.
• Explain how you would like to know their strategic priorities from the outset so that you can best represent these in later dialogues with the team.
• Challenge them on how their current career success has been forged on personal involvement - state that this is one of these moments where their expertise could be helpful.

In the case of delegation, don’t worry. The important point is to keep your C-level contact looped in throughout the buying cycle. Take the opportunity to share key meeting insights with them after every key engagement via email or using a technology like GetAccept, where you can track what areas of the material they are viewing and if they share the material with any other stakeholders internally.

A strategy that has also worked for me to keep less senior stakeholders happy, whilst I’m maintaining a C-level relationship, is to send emails complimenting their candour and ability in the C-level role, with them as Bcc. Not only can this make you popular at the lower level, but C-levels always enjoy affirmation that their team is representing the company in a professional manner.

Now that this is done look out for my next ebook where we discuss the steps involved in closing your deals!

– Dailius Wilson