CIO 101 for Entrepreneurs (2016)

1
IT Infrastructure Strategy for a Small
Businesses: CIO 101 for Entrepreneurs
Sept 8, 2016

Today’s Agenda
Module 2: IT Business
Systems
Discuss best practices
regarding strategic
planning for your
technology
infrastructure
Homework: Use the
provided Technology
Strategy Template to
create your
Technology Strategy
Module 1:
Technology Strategy
Questions to ask
before selecting a
System
About Mike
Introduction
Review IT Business
Systems, by
category and
maturity level
What we won’t cover today? (Due to time constraints)
Answer specific questions about
your company (Remember, you can
schedule one-on-one meetings
with me)
Detailed discussions about specific
products, vendors, or organizations

Graduated from Johns
Hopkins with a Masters
in Information Systems
JHU
CTO Adventures
• Promoted to CTO
• PMP certification
• PMI-ACP Agile certification
• Finalist for the 2012 NVTC
GovCon CTO Innovator
Award
• Obtained CMMI ML3 for
Halfaker (Business Process
Architecture)
• Agile Scrum transformation
of Internal IT, Quality
Mngmt., and Solutioning
teams
• Created Contracts
Compliance function
UVA
Graduated from UVA
with Bachelors in
Computer Engineering;
Joined Lockheed
Martin (Security
Engineering)
2003
2008
2008
2010
to
2016
About Mike
Halfaker
Joined Halfaker and
Associates at Director
of Operations (Ops, IT,
BD)
Disclaimer: Opinions expressed are solely my own and do not
necessarily reflect the views or opinions of Capitol Post or
Halfaker and Associates.

Veterans, thank you for your Service!

Module 1: Technology Strategy and Governance
“A satisfied
customer is the
best business
strategy of all.”
- Michael LeBoeuf

Components of Technology Strategy and Governance
Goals and Governance
Plans
Templates and Forms
Processes, Policies,
and Guidelines
Enterprise
Architecture
Databases and
Trackers

Strategy Section 1: Strategic Goals
• Identify your 1-3 business goals and
1-3 technology objectives
– Think about goals that define what you your
company to be in the future (vision), what your
company is and what it isn’t (mission), or
define your culture (values)
– Ensure that your technology objectives directly
support your business goals
Goals and Governance

Strategy Section 2: Enterprise
Architecture
• Draw or list the technology business
systems you have today
Example EA List
• Email (Google Apps)
• Website (GoDaddy)
• Dropbox
• 3 Dell laptops
• 2 Android smartphones
Enterprise
Architecture

Aligns with Biz Model?
Aligns with your Systems?
Does this system align with how you
do business or want to do business?
Does this system integrate with your
other systems?
Lock In?
Will you be stuck with this
vendor after this decision?
Can you export your
information?
Investment Return?
Is this system worth your
time and money? How about
the time it will take your
employees or customers to
adapt to it?
Consider True Cost of
Ownership (TCO), not just
initial price
Get Traction?
Will your employees and/or
customers actually use this
system?
No Big Risks?
Secure? Support?
Is your company’s information
secure? Will you be in the
newspaper for getting hacked,
based on this decision? Who will
support you if this breaks?
Will this System ALIGN with my Company?
The systems and processes and you
choose today will impact your
company for years to come –
so choose wisely!

Strategy Section 3: Plans
• Write in the upcoming calendar quarter boxes what
your technology priorities will be for each one
• Here’s an example:
4Q2015 1Q2016 2Q2016 3Q2016
• Move email
to Google
Apps
• Select and
buy a CRM
system
• Create and
publish IT
process for
new hires
• Redesign company
website, using a
professional
designer
Plans

Strategy Section 4:
Processes
• 1-800-GOT-JUNK scaled
from 1 franchise in 2000
to 270 in 2007
• “In 1996, I read Michael
Gerber's The E-Myth, and
it taught me that people
don't fail; systems do,” -
[Founder Brian]
Scudamore”
• Scudamore wrote down 1-
page processes (or
checklists) for every
important process
• See http://www.inc.com/magazine/201403/leigh-
buchanan/1-800-got-junk-business-model.html
Processes, Policies,
and Guidelines

Strategy Section 5: Templates,
Forms, and Checklists
• You may need to create templates and
forms to formalize how things happen
internally, or with customers
• Examples are:
– New Hire Checklist
– Project Kickoff Template
– New Customer Checklist
– Deliverable Checklist
– Purchase Request Form
• ACTION: List any templates, forms, or
checklists you know you need to create
ASAP
Templates and
Forms

Strategy Section 6: Databases
and Trackers
• As your company grows, you can’t keep
everything in your head or email
– “Your head is for having ideas, not for
holding them” – David Allen
• You’ll want to track critical information
somehow using spreadsheets, Google
Sheets, databases, SharePoint lists, or
something similar
• Things you may want to track:
– Projects (Who is assigned to which project?)
– IT Equipment (Who has which laptop, and
when does their warranty run out?)
– IT Access (Who has what level of access to
what Business Systems?)
– Software Licenses (How many copies of
Microsoft Office do we own? Who has
Adobe Acrobat Professional?)
Databases and
Trackers

Module 1 Exercise
Create your Technology Strategy, drafting your goals,
objectives, EA, and priorities (Sections 1 – 4)

Module 2: Business Systems Tour
“The salesman
knows nothing of
what he is selling
save that he is
charging a great
deal too much for
it.”
- Oscar Wilde
ML1 ML2 ML3

Business System Map
Organization Maturity
Business System Type ML1 ML2 ML3
Reporting
 Business
Dashboard
HR and Recruiting  HRIS  ATS
Finance and Accounting
 Back Office Ops
 Accounting
 Invoicing
Business Development, Sales,
and Marketing
 Company Website
 Accept Online
Payments
 Appointment Mngmt.
 Social Media
 CRM and Pipeline
 Sales Intelligence
Communication, Content, and
Collaboration
 Email
 Content and Doc.
Mngmt.
 Project / Task
Management
 Collaboration
Platform
Security  Anti-Virus (AV)
 Firewall/Router
 Computer Encryption
 Employee
Security
Training
Technology Infrastructure
 Internet
 Computers
 Phones
 Conferencing
 Printers
 External IT Support
 Mobile Device
Mngmt.
 Backups
 Network
Monitoring
 Identity
Management
ComplexityandStrategicValue

Maturity Level 1
“Technology is
anything that
wasn’t around
when you were
born.”
- Alan Kay (Computer
Scientist)
ML1

Infrastructure: Internet
Solutions Vendor(s) Est. Cost Notes
Business Internet
Service
(Recommended)
 Verizon Business
Internet (e.g. Fiber, DSL)
 Comcast
 CenturyLink
 MegaPath
 $400/mo.
For 3Mbps
 $1,200/mo.
For 10 Mbps
 $2,300/mo.
for 100 Mbps
 Ideal if available
 May take months to get internet
in your office, depending on
building management
 Shared Network (e.g. Comcast
Cable) is much cheaper than
dedicated, but the quality is not
consistent
Internet Service
Broker
 Cogent Communications
(http://www.cogentco.co
m)
 Can be helpful in identifying
options, at no explicit cost to
you
 Don’t always offer unbiased
advice
4G Cellular Hotspot
 Clear by Sprint
 Verizon Hotspot
 $50/mo.
with data cap
(e.g. 1GB
 Mobile and office-based options
are available
 Convenient, but can become
very expensive based on usage-
based pricing
 Internet connectivity is an essential service, which becomes
increasingly important as your grow as a company
 Consider identifying a vendor that can increase speed as you grow
 Consider how much you’ll rely on cloud services for other business
systems – more cloud means more internet bandwidth needs
ML1

Infrastructure: Computers
Issue employees
Windows-based
laptops
(Recommended)
 Lenovo (e.g. T400
series)
(Recommended)
 Dell (e.g. E5470)
(Recommended)
 HP
 $400 for
used
 $900 for
new
 Lenovo laptops are tough, but a
little more expensive (made in
China is concerning to some)
 Dell offers solid value
Issue employees
Mac laptops
(Recommended)
 Apple MacBook
laptops
(Recommended)
 $1,500
new
 Fewer options regarding Device
Management
 More expensive per machine
 May offer more convenience,
more durable machines, and
more security
Leverage BYOD and
subsidize employee
laptops
• N/A
• None or
Empl.
Subsidy
 May work well if employees are
tech-savvy, but can make IT
support difficult based on
different computer types
Use Virtual Desktop
Infrastructure (VDI)
and issue employees
thin clients
 Amazon WorkSpaces
 MSP-based offerings,
like iCore
 AWS WS
is
$35/mo.
 Varies
widely
 Can be powerful, but requires
very fast bandwidth and
advanced administrators
 While tablets are hot, computers continue to be the foundation of
employee technology
 Wirecutter.com has great, current, detailed reviews of technology
equipment, including laptops
ML1

Infrastructure: Phones
Bring Your Own
Device (BYOD)
 Several, such
as Dialpad or
Grasshopper
 Dialpad:
$15/user/m
mo.
 Offers convenience and reduced
management at potential cost of
security – see MDM
 You can subsidize monthly personal
phone costs with a stipend
 For leaders, you may want to issue a
phone so you can own the telephone
number (in case of employee
transition)
Company-issued
Smartphones
 Provider:
Verizon, AT&T,
Sprint, T-
Mobile
 Phone Type:
iPhone vs.
Android
 $50 per
month per
line
 Verizon is expensive, with excellent
coverage
 Issuing cell phones requires oversight
regarding minutes, data, and repair
support
 Android’s device and OS
fragmentation is a weaknesses for
enterprise environments
VoIP Landline
Phones
 Vonage
 RingCentral
 MegaPath
 $30 per
month per
line
 Commodity service – top-tier brands
offer similar price and features
 Telephones are still essential to business, and the trade-off between
BYOD and company-supplied is a significant decision regarding
management complexity, employee convenience, and security ML1

Security: Anti-Virus (AV)
Security Essentials  Microsoft  Free
 Great, free solution for Windows-based
computers
Intune Endpoint
Protection
 Microsoft
 $6 per
user per
month
 Included some Mobile Device Management
(MDM) capabilities, which is discussed
more in ML2
Avast Cloud-based
Antivirus
 Avast  Free
 Other good option (See
http://www.tomsitpro.com/articles/avast-
for-business-free-smbs,1-2473.html for
details)
WebRoot or ESET  Varies  Varies
 While Apple computers are less vulnerable
to malware than Windows, you may still
want to invest in it for users, especially
ones that are not tech-savvy and may use
their laptops outside of work (vulnerable to
phishing and other malware)
Malware Protection
 Malwareb
ytes
 $30 per
user per
year
 Useful to protect advanced attacks (think
ML2)
 See http://lifehacker.com/10-malware-
removal-apps-tested-malwarebytes-comes-
out-1614046598 for details
 Secure computers is essential to protecting your employees,
information, and infrastructure
ML1

Communication, Content,
and Collaboration: Email
 Microsoft
 $5-20 per user per
month
 Strong offering that includes
several collaboration tools,
including Exchange, SharePoint,
Skype (formerly Lync), OneDrive,
and Office Online
 Recommended over other
Exchange hosting providers
 Google
 $5-10 per user per
month
 Strong offering that includes
several collaboration tools,
including Gmail, Hangouts,
Calendar, Drive, Docs, Sheets,
Forms, Slides
Consumer Email
(e.g. Gmail, POP3,
IMAP)
(Not recomm.)
 Google (gmail)
 Hotmail
 Yahoo mail
 Comcast
 Free or Cheap
 Not recommended, due to lack
of professional functionality and
ability to completely map to
company domain name
 Business email choices are primarily driven by two offerings for
small businesses – Office 365 for Microsoft-centric organizations and
Google Apps for Google-centric organizations
 Choice should be driven by customer experience and employee
population
ML1

Infrastructure: Tele/Web Conferencing
Conferencing as part
of your
Collaboration /
Email Package
 Microsoft (Skype for
Business)
 Google (Hangouts)
 N/A
(Included
in Pkg.)
Web Conferencing
 GoToMeeting
 WebEx
 Speek Pro
 UberConference
 $40 per
month
per
account
(GoTo /
WebEx)
 Often capped at 25 or 40
concurrent users
Teleconferencing
 Unlimited
Conferencing
 6.5 cents
per
minute
per caller
 Can include 800 number access,
more professional greetings,
and more features (e.g. Find
out who is on the call; Record
call)
Free
Teleconferencing
 FreeConference.com  Free
Free Web
Conferencing
 Join.me  Free
 Up to 10 participants, Up to 5
video feeds
 Being able to set up teleconferences (multiple callers on one call)
and web conferencing (to screenshare and collaborate) is critical to
many organizations ML1

Infrastructure: Printers
Enterprise Tabletop
Printer
 HP (Recomm.)
 Ricoh
 Canon
 Est. $1,200
(B&W)
 Est. $1,500
(Color)
 Enables network printing
 Recommended for up to 10,000 pages per month
 For B&W laser printer, approximately 1.5 cents
per page
 For Color laser, approximately 13 cents per page
Managing Print
Services
 CentricBiz.com
 Varies by
package
 You pay per-page-printed, instead of buying
toner; and they provide printer maintenance and
toner
Consumer Inkjet
Printers
 Epson
 HP
 Canon
 Approx.
$100
 Good choice if you print less than 250 pages per
month
 Check TheWireCutter.com for a current
recommendation, based on your needs
Enterprise
Standalone Printer
 HP
 Ricoh
 Canon
 Est. $4,000
 Enables network printing
 Recommended for 10,000+ pages per month
 Can track/manage printing by user/project
 Buying cheap printers can end up being very expensive over the life
of the printer, considering toner, repairs, and printer longevity
 It is often true that expensive printers have cheap toner and cheap
printers have expensive toner/ink
 Double-sided printing can save you money in paper
 For simple hardware recommendations, check out
www.thewirecutter.com
ML1

BD/Sales/Marketing:
Company Website
Content as a Service
 Squarespace
(Recommended)
 $8-36 per
month
 Convenient, fast, enables do-it-
yourself approach
 Can upgrade to sell items (e-
commerce) through your site
Managed CMS
 Wordpress.com
 Drupal Gardens
 $8-80 per
month
 Enables more customization
than offerings like Squarespace,
while still leaving security
patching and maintenance
issues to the service provider
“Blank Slate”
Hosting
 GoDaddy
 Bluehost
(Recommended)
 Rochen
 $5-25 per
month
 Enables custom, high-end,
professional design
 You can solicit web design
support from design
outsourcing firms such as
99designs to obtain
professional, custom websites
 The design and hosting of your organization’s website is a critical
decision to how your organization will be seen by people outside the
organization
ML1

BD/Sales/Marketing:
Accept Online Payments
Solutions Est. Cost Notes
Square  2.75%
 Industry leader in modern mobile payment
system
PayPal  Starts at 2.7%
Industry-specific Payment
Systems
 Varies
 Several manufacturers offer industry-specific
payment systems for verticals such as
restaurants
 The best approach to accepting online payments varies wide, based
on what you’re selling
 For selling products in-person, here are some options:
ML1

Accept Online Payments
(Continued)
Squarespace
 $26 per month + credit card
fees
 Convenient, fast, enables do-it-yourself
approach
 Can upgrade to sell items (e-commerce)
through your site
Paypal  2.9% + 30 cents per transaction  Flexible, industry-leading platform
Shopify
 $29 per month + credit card
fees
 Industry-leading brand that provides an
annual entrepreneurship competition
Gumroad  5% + 25 cents per transaction
 Popular for selling information products, such
as e-books
Amazon.com  Varies  Huge audience in exchange for higher fees
 For selling products online, here are some industry leaders:
 For selling services, including recurring subscription fees:
ML1
Chargify
 $129/mo for up to 500
recurring customers
 Proven platform, strong analytics capabilities
Recurly  $100/mo + fees
Stripe  2.9% + 30 cents per transaction
 Built for developers to integrate into other
websites (not self-standing platform)

• Another option, instead building your own back
office (e.g. HR, Finance, Recruiting, Contracts)
operational capabilities is to out-source it to one or
more vendors or leverage a partner’s back office
capability
ML1
Option Vendor(s) / Options
Outsource some or all of your
Back Office functions to a
commercial service
 GetBackOps.com (Startup-focused Back Office support), uses tools
like QuickBooks, Bill.com, Box, PayChex, and Expensify to
automate back-office
 TriNet (HR outsourcing)
 iQBackOffice.com
 BOOST (boostllc.net, focused on GovCon)
 PEO (See upcoming HRIS slide)
Share Back Office capabilities with
a partner
 Leverage the SBA Mentor-Protégé Program (MPP), where mentor
can support back-office functions without GovCon affiliation (see
https://www.sba.gov/content/mentor-protege-program)
Multiple: Back Office Operations
and Administration

Finance and Accounting:
Accounting
Small Business
Software as a
Service (SaaS)
 QuickBooks Online
(Recommended)
 FreshBooks
(Recommended)
 $8-30 per
month
 SaaS model offers updated, web-
based software
 QuickBooks is along-time leader in
this category
 FreshBooks focused on convenient,
intuitive user interface
Small Business
Computer Software
 QuickBooks
 Microsoft Office
Accounting Express
 $200
 QuickBooks is classic choice within
small business accounting
Outsourced
Accounting Service
 Your Part-Time
Controller
 Boost, LLC
 Large
initial and
recurring
costs
 Outsources accounting function
Enterprise, Industry-
agnostic
 Microsoft Dynamics
GP
Enterprise, Industry-
specific
 Deltek GCS Premier
 Powerful functionality for
Government Contractors,
especially once they start
managing Cost Plus contracts
 Accounting systems are not glamorous, but they are essential to
effective business management
 Selecting the right system, and configuring the system with key
decisions like General Ledger structure are important decisions that
may haunt you for years to come if done poorly
ML1

Finance and Accounting:
Invoicing
Freshbooks  FreshBooks
 $8-30
per
month
 FreshBooks focused on convenient,
intuitive user interface
 Over five million people use
FreshBooks
Wave Invoicing  Wave  Free
 Tracks recurring payments
 Can track when invoices are viewed
 The price of free is its most
appealing feature
Harvest  Harvest
 Free to
$99 per
mo.
 Can create and track retainers
 Integrates with Trello, PayPal, Stripe,
Zendesk and Salesforce
 Creating, sending, and tracking invoices can become unwieldy
quickly
 For more details, check out
http://www.entrepreneur.com/article/246197
ML1

HR and Recruiting: HRIS
HRIS/Paycheck
Service Firm
(Established)
 ADP (Industry Leader)
 Paychex
 Ceridian
 Varies
greatly
depending
on options
and size
 Firm helps you manage payroll
and other HR tasks, but does
not assume HR responsibility
like a PEO does
Professional
Employer
Organization (PEO)
 AlphaStaff (large,
established PEO)
 TriNet
 Justworks (Startup-
focused PEO)
 Justworks
is $75 per
month per
employee
 Firm that you can outsource
employee management tasks
(e.g. benefits, payroll, workers’
comp, recruiting)
 Provides compliance reporting
support (e.g. EEO Reports)
 700 PEOs in the US, covering
about 3 million workers
 Liability is on PEO
HRIS/Paycheck
Service Firm
(Startup)
 BambooHR
 Wave Payroll
 Zenefits (Avoid)
 Wave is $4
per
employee
per month
+ $15/mo.
 Zenefits has an aggressive
approach to payroll integration
(think Uber) that creates
significant integration risks (see
https://news.ycombinator.com/i
tem?id=9679312)
 Your Human Resources Information System (HRIS), including
managing employee information, benefits information, and payroll is
essential to effectively growing your organization ML1

Maturity Level 2
“All of the biggest
technological inventions
created by man – the
airplane, the automobile,
the computer – says little
about his intelligence, but
speaks volumes about his
laziness.”
- Mark Kennedy (Author)
ML2

ML2
Infrastructure: MSPs
Full-service MSP
(Recommended)
 mindSHIFT
 iCore Networks
 Network Depot
 See next
slide
 If you are growing quickly
and/or don’t want to invest in IT
support staff, this can be a cost-
effective option for under 75
employees
Technology Resellers  CDW
 Most
services
are free
 May provide free solution
support, based on company
size, though biased toward in-
house solutions
None (No
Outsourced IT
Support)
(Recommended)
 N/A
 See next
slide
 If you have technical personnel
in house, this can be an
effective way to reduce cost and
maintain control
 Managed Service Providers (MSPs) enable you to outsource your
Technology operations, at a cost
 The advantage is convenience, the disadvantage is control and cost –
you may be migrated to a suite of solutions that don’t align with
your goals
 For more information, please see http://tinyurl.com/czbjbdq (“What
are MSPs?”)

ML2
External Support Decision Analysis
Course of Action Est. Annual Cost Notes
1: Hire full-time Junior
Technology Associate to keep
things running, add a new
system here or there
$75K
 Assume salary of $50K for college graduate
with IT degree
 Assume 1.5 no-fee, indirect wrap rate
2: Hire a full-time engineer
with 5 years of experience and
turn him into your head of
internal IT
$120K
 Assume salary of $80K for 5 years of
experience
 Assume 1.5 no-fee, indirect wrap rate
3: Contract with a MSP to get
IT support
$59K
 Assume $500/month management fee
 Assume $75/month desktop support per-
person fee for 20 employees
 Assume you pay $100 per hour for a IT Help
Desk Assoc. on-site, one day per week
 Assume $2,000/year in strategic
consulting/support (new projects / analysis)
 Assume you pay for consulting support to
setup 10 laptops per year at $300 each
 Assume 10% G&A load on expenses
 Comparing costs for technology talent and support is challenging
 This list doesn’t include expenses for buying equipment (e.g. laptops
for employees) or recurring technology expenses (e.g. email service)
 You can have an employee do part-time support, or combine some
MSP support with some internal support

ML2
Infrastructure: Mobile Device
Management (MDM)
AirWatch  VMWare
 $4-11 per
device per
year
 AirWatch supports Windows,
Android, iOS, Mac OS X, and
BlackBerry
 Gartner-rated Leader
Good Technology  Good  Unknown  Gartner-rated Leader
Maas360  IBM
 $0 – 15
per user
per month
Intune  Microsoft
 $6 per
user per
month
 Integrates well with Office 365
 Smartphones and laptops can be managed using Mobile Device
Management (MDM) software to enforce security policies and
protect sensitive company data
 MDM can separate work and personal data on smartphones
 Gartner now refers to MDM as Enterprise Mobility Management
(EMM)
 For discussions on startups and other options, see
https://www.quora.com/Mobile-Device-Management

ML2
Mobile Device Management (MDM)
Magic Quadrant
 Here’s the 2016
Gartner Magic
Quadrant for
Enterprise Mobility
Management, which is
what Gartner is
currently calling MDM
(Google Image Search
“2016 EMM Magic
Quadrant”)

ML2
Infrastructure: Backups
Cloud Backup
Service
 Backblaze (Recommended
for laptops and desktops)
 $50 per
computer per
year
 See Backblaze’s
comparison of services
https://www.backblaze.c
om/best-online-backup-
service.html
 Carbonite
 $60 per
computer per
year
 Mozy
 Depends on data
usage
 Crashplan  Depends on data
Employer-
managed
Cloud Backup
Software
 CloudBerry, using AWS
(Recommended for servers)
 Varies based on
storage usage
 Microsoft Backup Utility
(connected to a local
Network-Attached Storage
(e.g. Synology) or server)
 Free (Synology
hardware varies)
 Backing up your information is critical – hard drives fail, laptops and
computers are stolen, and people make mistakes
 Investing in backup solutions is like investing in insurance: You hope
you don’t need it often, but you will need it

ML2
Security: Firewall/Router
Cisco Meraki
Firewall Router
 Cisco  $600+
 MX65 supports 50 devices
($600)
 MX84 supports 200 devices
($2,000)
Juniper Firewall and
Router
 Juniper SSG series is
recommended
(http://www.juniper.n
et/us/en/products-
services/security/ssg-
series/)
 $1,000+
 It’s important to invest in a
network router and not just a
cheap router/wireless access
point when growing an
organization beyond a few
employees
Cisco Firewall and
Router
 Cisco
 Varies
widely
WatchGuard Firewall
and Router
 WatchGuard (Not
recommended)
 $500+
 As your organization grows, it’s important to protect your network
for your network infrastructure (office locations)
 Your network should have a firewall protecting it, in addition to
using computer-based firewalls (e.g. Microsoft Windows Firewall)
 It’s imperative that a firewall is in between your internet connection
and your network router or wireless access point

ML2
Security: Computer Encryption
Operating System
Encryption
 Microsoft Windows
BitLocker (Available in
some versions of
Windows 7, 8, and
10)
 Apple Mac FileVault –
available as of OS X
10.3 (Rel. Oct 2003)
 $99 to
upgrade
to MS
Professio
nal
 Free on
Mac
 Can encrypt removable hard
drives and thumb drives
Symantec Endpoint
Protection
 $25/user/
year
Open Source  VeraCrypt  Free
 A critical measure of security is to ensure that data stored on physical
devices is encrypted (often referred to as “Whole Disk Encryption”
 Think about encryption for all your devices, including:
 Laptops
 Smartphones
 Tablets
 External (USB) hard drives
 USB “thumb drives”
 Your computer password is easy to get around, and is not a solid defense

ML2
Comm., Content, and Collab.:
Document Management
Microsoft-centric
Document
Management
 SharePoint Online
(Part of Office 365)
(Recommended)
 Part of
O365
Google-centric
Document
Management
 Google Docs (Part of
Google Apps)
(Recommended)
 Part of GA
File Server or
Network Attached
Storage (NAS) device
 Microsoft Windows
Small Business Server
 Synology NAS
 Varies
based on
data
 Requires local
management/administration
 Requires VPN configuration if you
want to access it outside your
local network
Cloud Service
 Box.com (Enterprise-
focused)
 Dropbox (Consumer
and small business-
focused)
 Bitrix
 Varies
based on
data and
users
 Various levels of configuration
management and functionality
 Dropbox announced integration
with Microsoft Office
 Sharing and publishing documents is a key capability as your grow
 Convenience and configuration management (version control) are
key characteristics to consider
 Structure and governance is very important – maintaining sites,
folders, and permissions get much harder as you grow

ML2
Communication, Content,
and Collaboration:
Project / Task Management
Basecamp
 Basecamp (formerly
37signals)
 $20 per mo. (Up
to 10 projects)
 Great for simple project / task
management
 Also check out Asana
Trello  Trello
 Free (Advanced
available @ $3.75
/ user / mo.)
 Spun out of Fog Creek Software
 Great, card-based, Agile-inspired
task management system
JIRA Agile  Atlassian
 $10 per month for
10 users
 Based on Agile software
management concepts
 Able to scale to larger projects
effectively
 Similar to VersionOne, Rally, and
Pivotal Tracker
Slack  Slack
 $0 – 12 per user
per month
 Collaboration platform for team
collaboration
Traditional Project
Management Systems
 Microsoft Project
Online
 Varies (can be
rented through
O365)
 See also MS Team Foundation
Server
 Managing tasks across projects and departments, outside of email
and meetings, is a critical part of an organization growing in size and
complexity

ML2
BD/Sales/Marketing: Social Media
Hootsuite  Hootsuite  Free
 Enables posting content to
multiple platforms, shows
search filters, etc.
 Can schedule posts for future
times
Buffer  Buffer  Free
 Can schedule posts for future
times
 Investing in social medias that are relevant to your customers
 Consistent usernames across social media platforms is a best
practice
 Books like Groundswell and Platform provides a solid strategic
framework to consider social media marketing
 Consider a hub-and-spoke model where you publish content to your
company’s website and market it through email blasts and social
media posts

ML2
BD/Sales/Marketing: CRM and Pipeline
Pipedrive  Pipedrive
 $12 per
user per
month
 Pipedrive includes pipeline
modeling
Insightly  Insightly
 Free for 2
users
 Strong option with free 2 user
level
Highrise  Basecamp
 $24 / mo.
for up to 6
users
 Highrise is lean and simple
Excel-based Pipeline
Tracker
 N/A  None
 Can be tailored to project
pipeline at no recurring cost,
but can quickly become
unwieldy
Enterprise CRM with
Pipeline Tracking
 Salesforce
 Microsoft Dynamics
CRM
 SugarCRM
 $25 - $250
/usr. / mo.
Salesforce
 Salesforce and Dynamics lead
the enterprise CRM space
 Salesforce is free for non-profits
 SugarCRM is open source
 Customer Relationship Management (CRM) tracks your business
contacts, including sales leads and partners, including contact
information and contact history
 Enterprise CRM systems also track sales opportunities and sales
pipeline
 Great discussion on Quora at https://www.quora.com/What-is-the-
best-CRM-software-for-startups

ML2
BD/Sales/Marketing: Sales Intelligence
Solutions Vendor(s) Est. Cost
GovWinIQ (Government
Contracting Industry)
 Deltek  Expensive
Bloomberg Government
(GovCon)
 Bloomberg  Expensive
Other GovCon Solutions
 EZGovOpps
 Govini
 AlphaBrook.com
 GovTribe.com (startup)
 Varies
Sales Intelligence
Communities
 Example: G2Xchange.com (Federal Government
Contracting Health IT community)
 $250 per user
per year
Buying Email Lists and
Leads
 DiscoverOrg.com – provides IT organization
charts and contact data
 Radius.com – reach small business leaders
 Varies
Free Sales Intelligence
 Search alerts from free websites (e.g.
FedBizOpps.gov, Federal Agency Acquisition
Forecasts)
 Collect website visitors’ email addresses, in
exchange for downloading a whitepaper or other
document
 None
 Sales Intelligence tools and subscriptions can be powerful ways to
buy leads, especially for industries that traditionally required a large
sales force
 Talk to people in your industry and check out relevant discussions
online -- sales intelligence tools vary widely by industry

Maturity Level 3
“Any sufficiently
advanced
technology is
equivalent to
magic.”
- Arthur C. Clarke
ML3

ML3
Infrastructure: Network Monitoring
Firewall-based IDS/IDP
(Recommended)
 Cisco Meraki is easy to use;
but isn’t the cheapest and
requires annual subscription
 Cisco Sourcefire is industry
leading (not cheap)
 Cisco Meraki MX84
is 200 device
firewall/router/IDS
for $2,000
 Varies widely
 Firewall/Router-based
Intrusion Detection and
Intrusion Prevention
Systems are great ways
to leverage existing
hardware
IDS/IDP Monitoring
Appliance
 Soltra Edge
 Barracuda
 FireEye
 Vectra Networks
 Varies widely
Open Source IDS/IDP
Monitoring
 Snort
 Security Onion
 “Free”
 Requires hardware,
configuration expertise,
and administration
Web Proxy
 Zscaler (Cloud Service)
 McAfee Web Gateway
(Device)
 Blue Coat ProxySG (Device)
 $5-15/user/month
for Zscaler
 Approx. $6K for
McAfee WG
 Analyzes and protects
web traffic, in real-time
Security Information
and Event
Management (SIEM)
Tool
 HP ArcSight
 Splunk
 McAfee NitroSIEM
 Expensive
 Aggregate and analyze
security information
from servers, firewalls,
routers, etc.
 Actively monitoring your network for cyber security anomalies is a
key investment in protecting your company’s information, including
customer and partner information

ML3
Infrastructure: Identity Mngmt.
Active Directory-
centric
 Microsoft Active
Directory
(Recommended)
 “Free”
with
Windows
Server
 Can be federated (sync-ed) with
Office 365
Google Apps-centric
 Google Apps
(Recommended)
 Ping Identity
 Centrify
 “Free”
with
Google
Apps
 Google Apps is becoming an
identity standard
Distributed Single
Sign On
 Okta
(Recommended)
 OneLogin
 ClearLogin
 $2-8 per
user per
month
(Okta)
 Several companies offer
distributed, consolidated single
sign-on (SSO) solutions
Enterprise Password
Management
 LastPass
 Distributed SSO
solutions (see above)
 $12-24 per
user per
year
 Instead of centralizing identity
itself, you can deploy an
enterprise password
management system
 You can also consider local
computer-based KeePass
 As your organization obtains more and more business systems, it will
be important to manage identity through a central Identity and
Access Management (IdAM) system or enterprise password
management system

ML3
Security: Employee Security Training
Computer
Security
Employee
Training
 N/A  Free
 Train all your employees in Computer
Security Fundamentals, at least once a year
– you can Google for best practices (e.g.
Don’t download things or click on links from
places you don’t recognize, Update
software when computer prompts you)
Phishing Training
and Testing
 Many, such
as
PhishMe
 Expensive
(Think order
of
$10K+/year)
 Services like PhishMe provide phishing
training and also send phishing emails to
your employees to test their ability to
recognize them
Phishing IQ Test  SonicWALL  Free
 See
http://www.sonicwall.com/furl/phishing/
to test your own ability to recognize
phishing emails
 In addition to providing your employees with secure hardware and
maintaining the software, it’s important that you train your
employees in computer security
 A big trend in business cyber vulnerabilities is Phishing, which is
when a malicious email that looks legitimate tricks an employee to
click on a link or open an attachment, which then launches malicious
code on their computer
 Spear Phishing – Phishing targeted at individual, specific people

ML3
HR and Recruiting:
Applicant Tracking System (ATS)
JobVite.com  JobVite
 $500 per month
(<100 employees)
 Solid choice for small businesses
Lever.co  Lever
 Depends (e.g.
$800 per month)
 Well worth considering
Jazz (formerly
Resumator)
 Jazz
 $150 - $700 per
month
 Slick interface, but lacks
important reporting capabilities
Silkroad ATS  Silkroad
 Approx.
$5,000/year
 Comprehensive ATS, aimed at
mid-size businesses
SmartRecruiter.com
 Smart
Recruiter
 Starts at $3500
per year
ADP Recruiting  ADP
 Packaged with
ADP
 Not recommended, based on
poor user interface
Oracle Taleo  Oracle  Expensive
 Not recommended, based on
price
 An ATS is a valuable investment when you have more than one
recruiter to coordinate, or when you are willing to invest in
automating more of your sourcing and recruiting workflow

ML3
Reporting: Business Dashboard
QlikView  Qlik
 Varies
widely
 Data Discovery platform
Tableau  Tableau  Data Discovery platform
Spotfire  Tibco  Data Discovery platform
Impromptu  IBM Cognos  Traditional reporting tools to
automate report generationCrystal Reports  Crystal Reports
 Creating a consolidated, enterprise dashboard of your enterprise
business data is a valuable, though costly, proposition that can
enable better business decisions
 This is not a recommended priority for small companies with other
priorities to focus on
 This initiative must be pursued with a clear strategic framework, to
avoid wasted effort

Reporting: Business Dashboard
Magic Quadrant
Here’s the 2016
Gartner Magic
Quadrant for
Business
Intelligence and
Analytics
Platforms
ML3

Module 2 Homework
• Finish refining your Technology Strategy (using the
provided template, or another approach)

Wrap-up
“You're still here?
It's over. Go home.
Go.”
- Ferris Bueller

Top IT 101 Tips
1. Decide a strategy and make a plan, before you buy
technology – every decision affects your future IT
infrastructure, and you can save many headaches by thinking
through a plan before buying new technology
2. Look for answers and explanations on CIO, technology, social
websites, like Quora, YouTube, Lifehacker, Spiceworks, and
CIO.com
3. Don’t always pick the cheapest option – consider if this
solution will be able to grow with your company
4. Read books and blogs to learn best practices (but don’t let
that get in the way of running your business)
5. If it makes sense, consider paying for outsourced IT support
(Managed Service Provider) so you can focus on your
company
6. Connect with people who have IT experience at bigger
organizations (e.g. Meetups, Professional Organizations,
former colleagues)

Resources to Analyze Business Systems
Yourself
• Gartner Magic Quadrants (Google
“[Business System Type]
Magic Quadrant” – you can also
try adding “filetype:pdf” to the
end of the search string (top-right is
“best”)
• Check websites like Quora,
Lifehacker, and CIO.com for advice
• Asking colleagues and peers about
their experience

Assessing your EA and
Infrastructure
• If you want at a later time, you can rate your company’s infrastructure and
business systems by assigning red, yellow, or green to each of these aspects of
your organization
• Approach inspired by a mindSHIFT (Managed Service Provider) analysis process
Availability
Redundancy in
servers, network,
and power
infrastructure
Scalability
Consistency
(Limited Shadow
IT)
Identity
Management
Ability to grow
Business
Continuity
Business
Processes
Backups
Disaster Recovery
Internet
Redundancy
Information
Security
Network
Computer
Server
Mobile Devices
Policies,
Procedures, Plans
Cloud
Services
(SaaS)
Identity and
Access processes
and tracking
Secure Vendors
Scalable Costs
Enterprise
Architecture

Process is Key to Manageable Growth
IT Business Systems
IT Business Systems
Chaos
GrowthStrategy and Process
Strategy and
Process
With
With-
out

Questions?
• If you have any questions, please feel free to
contact me:
– mike@mikehking.com
– Twitter @mikehking
– Blog: www.mikehking.com (Slides will be
posted here)
• Thanks to Capitol Post for hosting!

CIO 101 for Entrepreneurs (2016)

Recommended

Recommended

More Related Content

What's hot

What's hot (20)

Viewers also liked

Viewers also liked (20)

Similar to CIO 101 for Entrepreneurs (2016)

Similar to CIO 101 for Entrepreneurs (2016) (20)

More from Michael King

More from Michael King (11)

Recently uploaded

Recently uploaded (20)

CIO 101 for Entrepreneurs (2016)